Herein,we present a copper-catalyzed carbonylative cross-coupling of unactivated alkyl bromides with aryl boronates under CO atmosphere which enabling the efficient synthesis of C(sp3)-C(sp2)ketones with extensive fun...Herein,we present a copper-catalyzed carbonylative cross-coupling of unactivated alkyl bromides with aryl boronates under CO atmosphere which enabling the efficient synthesis of C(sp3)-C(sp2)ketones with extensive functional group compatibility.This strategy represents a significant advance in copper-catalyzed carbonylation involving alkyl bromides and C(sp2)-nucleophiles.The protocol addresses key challenges commonly encountered in the coupling of C(sp3)-alkyl halides with aryl boron reagents,such as sluggish oxidative addition of alkyl halides,competing Suzuki-Miyaura cross-coupling,undesired dehalogenation and so on.Distinguished by its broad substrate scope and high functional group tolerance,this approach offers a robust and versatile platform for the streamlined synthesis of alkyl aryl ketones.展开更多
A convenient,efficient and practical metal-free method for the synthesis of substituted phenols from arylboronic acids has been developed.The protocol uses hydrogen peroxide as a hydroxylating agent ammonium bicarbona...A convenient,efficient and practical metal-free method for the synthesis of substituted phenols from arylboronic acids has been developed.The protocol uses hydrogen peroxide as a hydroxylating agent ammonium bicarbonate as an additive,and the reactions were conveniently performed in water at room temperature.The method shows an excellent tolerance of functional groups,so it will find a wide variety of applications in academic and industrial research.展开更多
Isotetronic acids are of great agricultural and pharmacological relevance and occur in a number of natural products. A convenient synthetic pathway to β-aryl substituted isotetronic acid derivatives was developed via...Isotetronic acids are of great agricultural and pharmacological relevance and occur in a number of natural products. A convenient synthetic pathway to β-aryl substituted isotetronic acid derivatives was developed via Suzuki cross-coupling of the corresponding β-bromo substituted isotetronic acid derivatives with arylboronic acids under palladium acetate catalysis. Good to excellent yields have been achieved展开更多
In this work, an efficient copper-catalyzed three-component reaction for the synthesis of sulfenylimidazo [1,2-a]pyridines using elemental sulfur as the sulfenylating agents has been developed. The reaction could proc...In this work, an efficient copper-catalyzed three-component reaction for the synthesis of sulfenylimidazo [1,2-a]pyridines using elemental sulfur as the sulfenylating agents has been developed. The reaction could proceed smoothly with a high degree of functional group tolerance and provide the desired products in moderate to good yield.展开更多
A novel and green nitrating reagent has been developed for the nitrification and nitration of arylboronic acids, which can be controlled by the reaction conditions. The process provides an attractive alternative to th...A novel and green nitrating reagent has been developed for the nitrification and nitration of arylboronic acids, which can be controlled by the reaction conditions. The process provides an attractive alternative to the traditional nitration protocols.展开更多
A manganese (Ⅲ)-promoted oxidative radical cascade reaction of easily accessible arylboronic acids with isocyanides to construct diimide derivatives was studied. This protocol provides a new way to synthesis of acety...A manganese (Ⅲ)-promoted oxidative radical cascade reaction of easily accessible arylboronic acids with isocyanides to construct diimide derivatives was studied. This protocol provides a new way to synthesis of acetyl diimide derivatives. New C-C, C-N and C=O bonds were formed in one step.展开更多
Herein,we report the first Rh~Ⅲ-catalyzed regioselective C8 arylation of quinoline N-oxides with commercially available arylboronic acids as coupling partners.This procedure is simple,and the reaction shows perfect r...Herein,we report the first Rh~Ⅲ-catalyzed regioselective C8 arylation of quinoline N-oxides with commercially available arylboronic acids as coupling partners.This procedure is simple,and the reaction shows perfect regioselectivity,a broad substrate scope,and isolated yields of up to 92%.We demonstrate the utility of the reaction by using it for late-stage functionalization of a fungicide.展开更多
A novel palladium-catalyzed carbonylative cyclization of alkene-tethered indoles with phenols or arylboronic acids is described,which provides a facile approach to access indolo[2,1-a]isoquinoline scaffolds.This metho...A novel palladium-catalyzed carbonylative cyclization of alkene-tethered indoles with phenols or arylboronic acids is described,which provides a facile approach to access indolo[2,1-a]isoquinoline scaffolds.This method employs benzene-1,3,5-triyl triformate(TFBen)as the CO surrogate for the incorporation of a carbonyl group into indolo[2,1-a]isoquinoline scaffolds,and a variety of carbonyl-containing indolo[2,1-a]isoquinoline derivatives are prepared in good yields.展开更多
A novel polystyrene-supported triol resin was first prepared by reaction of the Merrifield resin with trometamol. Using this resin, arylboronic acids were efficiently isolated and purified through a ＂capture-release...A novel polystyrene-supported triol resin was first prepared by reaction of the Merrifield resin with trometamol. Using this resin, arylboronic acids were efficiently isolated and purified through a ＂capture-release＂ procedure in organic solvents. However, in basic aqueous solvents arylboronic acids were immobilized on the resin only with low yield. 2012 Tao Jiang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All fights reserved.展开更多
A Mn(Ⅲ) mediated radical reaction of new designed multi-functionalized 2-isocyano-6-alkenyl(alkynyl)benzonitriles with arylboronic acids has been developed.This reaction provides a method for the synthesis of pyrrolo...A Mn(Ⅲ) mediated radical reaction of new designed multi-functionalized 2-isocyano-6-alkenyl(alkynyl)benzonitriles with arylboronic acids has been developed.This reaction provides a method for the synthesis of pyrroloisoquinoline derivatives through the formation of two C-C bonds and one C-N bond via radical cascade cyclization in one step.展开更多
CuCl/Phen can catalyze the C–N coupling between arylboronic acid and benzofurazan1‐oxide.This reaction occurred under mild and redox‐neutral conditions with benzofurazan1‐oxide as an aminating reagent via ring sci...CuCl/Phen can catalyze the C–N coupling between arylboronic acid and benzofurazan1‐oxide.This reaction occurred under mild and redox‐neutral conditions with benzofurazan1‐oxide as an aminating reagent via ring scission,leading to a bifunctionalized aminonitrobenzene.展开更多
Direct C—H functionalization of quinoline N-oxides with arylboronic acids is achieved using KMnOas the sole and efficient oxidative system.This method provides an efficient protocol to construct regioselectively 2-ar...Direct C—H functionalization of quinoline N-oxides with arylboronic acids is achieved using KMnOas the sole and efficient oxidative system.This method provides an efficient protocol to construct regioselectively 2-arylquinoline N-oxides via radical cross-coupling reaction in moderated to good yields under mild conditions.展开更多
Although bromodifluoromethane （BrCF2H） is a simple and readily available fluorine source, direct formation of difluoromethylated arenes with BrCF2H has not been reported. Herein, we describe an efficient method to a...Although bromodifluoromethane （BrCF2H） is a simple and readily available fluorine source, direct formation of difluoromethylated arenes with BrCF2H has not been reported. Herein, we describe an efficient method to access difluoromethylated arenes through a nickel-catalyzed difluoromethylation of arylboronic acids with BrCF2H. The reaction exhibits high efficiency, good functional group tolerance and broad substrate scope, thus providing an efficient route for applications in drug discovery and development. Preliminary mechanistic studies reveal that a difluoromethyl radical is involved in the reaction.展开更多
A practical procedure for palladium catalyzed Suzuki cross-coupling reaction of arylboronic acids with aryl hal-ides, including aryl chlorides in molten tetra-n-butylammonium bromide (TBAB) was developed. The reaction...A practical procedure for palladium catalyzed Suzuki cross-coupling reaction of arylboronic acids with aryl hal-ides, including aryl chlorides in molten tetra-n-butylammonium bromide (TBAB) was developed. The reaction exhibits high efficiency and functional group tolerance. The recovery of the catalyst and molten n-Bu4NBr was also investigated.展开更多
A series of solvents were examined for the ligand free Pd（II）-catalyzed Suzuki reaction of 4-bromotoluene with phenylboronic acid. It was found that the PdCl2/i-PrOH system could efficiently inhibit the homo-couplin...A series of solvents were examined for the ligand free Pd（II）-catalyzed Suzuki reaction of 4-bromotoluene with phenylboronic acid. It was found that the PdCl2/i-PrOH system could efficiently inhibit the homo-coupling of phenylboronic acid and give a cross-coupling product in high yields. The substrates with a wide variety of functional groups were tolerated in the system. A possible mechanism for this system was proposed.展开更多
Immobilized copper（Ⅱ） in organic-inorganic hybrid materials catalyzed Ar-N coupling of arylboronic acids with imidazoles has been developed. Arylboronic acids reacted with imidazoles smoothly in the presence of a 3...Immobilized copper（Ⅱ） in organic-inorganic hybrid materials catalyzed Ar-N coupling of arylboronic acids with imidazoles has been developed. Arylboronic acids reacted with imidazoles smoothly in the presence of a 3-（2-aminoethylamino）propyl functionalized silica gel immobilized copper（Ⅱ） catalyst （10 mol%） in methanol without any additives and bases. The reactions generated the corresponding cross-coupling products in good yields. Furthermore, silica-supported copper can be recovered and recycled by a simple filtration procedure and used for five consecutive trials without decreases in activity.展开更多
A simple electrochemically mediated method for the conversion of nitroarenes to aryl boronic esters is presented.Electrochemical borylation of a diverse range of nitroarenes,including the late-stage borylation of bioa...A simple electrochemically mediated method for the conversion of nitroarenes to aryl boronic esters is presented.Electrochemical borylation of a diverse range of nitroarenes,including the late-stage borylation of bioactive molecules,is furnished at room temperature under simple conditions,thereby demonstrating the broad utility and functional-group tolerance of this protocol.This transformation provides a convenient and practical access to aryl boronic esters from widely available nitroarenes,which would significantly streamline the synthetic process of diverse functionalized arenes.展开更多
The direct coupling of allylic alcohols with arylboronic acids or their derivatives catalyzed by Ni（cod）2 in the presence of a catalytic amount of base has been developed. A wide variety of allylic substrates or ary...The direct coupling of allylic alcohols with arylboronic acids or their derivatives catalyzed by Ni（cod）2 in the presence of a catalytic amount of base has been developed. A wide variety of allylic substrates or aryIboronic acids turned out to be applicable to this catalytic system. The present method does not require the use of ligands for stabilizing the nickel catalyst in most cases or additional activators for activation of altylic alcohols.展开更多
The boron trifluoride induced Suzuki-Miyaura cross-coupling of aryltriazenes with arylboronic acids catalyzed by Pd（OAc）2 without added ligands has been achieved for the first time. The reactions performed at room t...The boron trifluoride induced Suzuki-Miyaura cross-coupling of aryltriazenes with arylboronic acids catalyzed by Pd（OAc）2 without added ligands has been achieved for the first time. The reactions performed at room temperature under an argon atmosphere give biaryls in good to excellent yields. It is noteworthy that the reactions were conducted under mild and ligand-free conditions.展开更多
Synthesis of triarylmethanes via metal-free reductive coupling of diaryl ketone, tosylhydrazide, and arylboronic acids has been developed. This methodology is realized via one-pot two-step reactions involving the prep...Synthesis of triarylmethanes via metal-free reductive coupling of diaryl ketone, tosylhydrazide, and arylboronic acids has been developed. This methodology is realized via one-pot two-step reactions involving the preparation of N-tosylhydrazones by reacting tosylhydrazide with diaryl ketone derivatives, followed by the reductive coupling with arylboronic acid in the presence of potassium carbonate to afford various triarylmethanes analogues in moder- ate to good yields. Importantly, the system presented here enables the use of easily accessible starting materials and a series of substrates with diverse functional group could be tolerant in this reaction. This approach could also be particularly useful for the synthesis of triaryl-substituted carbazolyl compounds.展开更多
文摘Herein,we present a copper-catalyzed carbonylative cross-coupling of unactivated alkyl bromides with aryl boronates under CO atmosphere which enabling the efficient synthesis of C(sp3)-C(sp2)ketones with extensive functional group compatibility.This strategy represents a significant advance in copper-catalyzed carbonylation involving alkyl bromides and C(sp2)-nucleophiles.The protocol addresses key challenges commonly encountered in the coupling of C(sp3)-alkyl halides with aryl boron reagents,such as sluggish oxidative addition of alkyl halides,competing Suzuki-Miyaura cross-coupling,undesired dehalogenation and so on.Distinguished by its broad substrate scope and high functional group tolerance,this approach offers a robust and versatile platform for the streamlined synthesis of alkyl aryl ketones.
基金the National Natural Science Foundation of China (No. 21105054) for financial support
文摘A convenient,efficient and practical metal-free method for the synthesis of substituted phenols from arylboronic acids has been developed.The protocol uses hydrogen peroxide as a hydroxylating agent ammonium bicarbonate as an additive,and the reactions were conveniently performed in water at room temperature.The method shows an excellent tolerance of functional groups,so it will find a wide variety of applications in academic and industrial research.
基金the Municipal Government of Shanghai (No.03DZ19209) and Shanghai Hua-Yi Group for financial support.
文摘Isotetronic acids are of great agricultural and pharmacological relevance and occur in a number of natural products. A convenient synthetic pathway to β-aryl substituted isotetronic acid derivatives was developed via Suzuki cross-coupling of the corresponding β-bromo substituted isotetronic acid derivatives with arylboronic acids under palladium acetate catalysis. Good to excellent yields have been achieved
基金supported by the National Natural Science Foundation of China(Nos.21072054,21572051,21602057)the Ministry of Education of China(No.213027A)the Scientific Research Fund of Hunan Provincial Education Department(No.15A109)
文摘In this work, an efficient copper-catalyzed three-component reaction for the synthesis of sulfenylimidazo [1,2-a]pyridines using elemental sulfur as the sulfenylating agents has been developed. The reaction could proceed smoothly with a high degree of functional group tolerance and provide the desired products in moderate to good yield.
基金support by New-Shoot Talented Man Plan Project of Zhejiang Province(No. 2011R429012)
文摘A novel and green nitrating reagent has been developed for the nitrification and nitration of arylboronic acids, which can be controlled by the reaction conditions. The process provides an attractive alternative to the traditional nitration protocols.
基金the National Natural Science Foundation of China(Nos. 21772137, 21672157, 21372174)the Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions (No. 16KJA150002)+2 种基金the Ph.D. Programs Foundation of PAPDthe project of scientific and technologic infrastructure of Suzhou (No. SZS201708)Soochow University for financial support
文摘A manganese (Ⅲ)-promoted oxidative radical cascade reaction of easily accessible arylboronic acids with isocyanides to construct diimide derivatives was studied. This protocol provides a new way to synthesis of acetyl diimide derivatives. New C-C, C-N and C=O bonds were formed in one step.
基金the National Natural Science Foundation of China(Nos.21977056,21732002,21672117,21602117,21772104,31760527)the Tianjin Natural Science Foundation(No.16JCZDJC32400)for generous financial support for our programs。
文摘Herein,we report the first Rh~Ⅲ-catalyzed regioselective C8 arylation of quinoline N-oxides with commercially available arylboronic acids as coupling partners.This procedure is simple,and the reaction shows perfect regioselectivity,a broad substrate scope,and isolated yields of up to 92%.We demonstrate the utility of the reaction by using it for late-stage functionalization of a fungicide.
基金the financial supports from the Joint Funds of the Zhejiang Provincial Natural Science Foundation of China(No.LTY21B020001)the Fundamental Research Funds of Zhejiang Sci-Tech University(No.2021Q052)。
文摘A novel palladium-catalyzed carbonylative cyclization of alkene-tethered indoles with phenols or arylboronic acids is described,which provides a facile approach to access indolo[2,1-a]isoquinoline scaffolds.This method employs benzene-1,3,5-triyl triformate(TFBen)as the CO surrogate for the incorporation of a carbonyl group into indolo[2,1-a]isoquinoline scaffolds,and a variety of carbonyl-containing indolo[2,1-a]isoquinoline derivatives are prepared in good yields.
文摘A novel polystyrene-supported triol resin was first prepared by reaction of the Merrifield resin with trometamol. Using this resin, arylboronic acids were efficiently isolated and purified through a ＂capture-release＂ procedure in organic solvents. However, in basic aqueous solvents arylboronic acids were immobilized on the resin only with low yield. 2012 Tao Jiang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All fights reserved.
基金the National Natural Science Foundation of China(Nos.21971174,21772137,21542015 and 21672157)PAPD,the Project of Scientific and Technologic Infrastructure of Suzhou(No.SZS201708)+1 种基金the Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions(No.16KJA150002)Soochow University for financial support。
文摘A Mn(Ⅲ) mediated radical reaction of new designed multi-functionalized 2-isocyano-6-alkenyl(alkynyl)benzonitriles with arylboronic acids has been developed.This reaction provides a method for the synthesis of pyrroloisoquinoline derivatives through the formation of two C-C bonds and one C-N bond via radical cascade cyclization in one step.
基金supported by the National Natural Science Foundation of China(21525208 and 21472186)Research Fund from Henan Normal University(5101034011009)~~
文摘CuCl/Phen can catalyze the C–N coupling between arylboronic acid and benzofurazan1‐oxide.This reaction occurred under mild and redox‐neutral conditions with benzofurazan1‐oxide as an aminating reagent via ring scission,leading to a bifunctionalized aminonitrobenzene.
基金supported by the Department of Henan Province Natural Science and Technology Foundation(No.142102210410)Natural Science Foundation in Henan Province Department of Education(No.17A150005)+1 种基金the Program for Innovative Research Team from Zhengzhou(No.131PCXTD605)Project of Youth Backbone Teachers of Henan University of Technology
文摘Direct C—H functionalization of quinoline N-oxides with arylboronic acids is achieved using KMnOas the sole and efficient oxidative system.This method provides an efficient protocol to construct regioselectively 2-arylquinoline N-oxides via radical cross-coupling reaction in moderated to good yields under mild conditions.
基金This work was financially supported by the National Natural Science Foundation of China （Nos. 21425208, 21672238, 21332010, and 21421002）, the Strategic Priority Research Program of Chinese Academy of Sciences （No. XDB20000000）, and SIOC.
文摘Although bromodifluoromethane （BrCF2H） is a simple and readily available fluorine source, direct formation of difluoromethylated arenes with BrCF2H has not been reported. Herein, we describe an efficient method to access difluoromethylated arenes through a nickel-catalyzed difluoromethylation of arylboronic acids with BrCF2H. The reaction exhibits high efficiency, good functional group tolerance and broad substrate scope, thus providing an efficient route for applications in drug discovery and development. Preliminary mechanistic studies reveal that a difluoromethyl radical is involved in the reaction.
文摘A practical procedure for palladium catalyzed Suzuki cross-coupling reaction of arylboronic acids with aryl hal-ides, including aryl chlorides in molten tetra-n-butylammonium bromide (TBAB) was developed. The reaction exhibits high efficiency and functional group tolerance. The recovery of the catalyst and molten n-Bu4NBr was also investigated.
文摘A series of solvents were examined for the ligand free Pd（II）-catalyzed Suzuki reaction of 4-bromotoluene with phenylboronic acid. It was found that the PdCl2/i-PrOH system could efficiently inhibit the homo-coupling of phenylboronic acid and give a cross-coupling product in high yields. The substrates with a wide variety of functional groups were tolerated in the system. A possible mechanism for this system was proposed.
基金Project supported by the National Natural Science Foundation of China （No. 20372024）, the Excellent Scientist Foundation of Anhui Province （No. 04046080）, the Scientific Research Foundation for the Returned 0verseas Chinese Scholars, the Ministry of Education of China （No. 2002247）, the Excellent Young Teacher Program of the Ministry of Education of China （No. 2024） and the Key Project of Science and Technology of the Ministry of Education of China （No. 0204069）.
文摘Immobilized copper（Ⅱ） in organic-inorganic hybrid materials catalyzed Ar-N coupling of arylboronic acids with imidazoles has been developed. Arylboronic acids reacted with imidazoles smoothly in the presence of a 3-（2-aminoethylamino）propyl functionalized silica gel immobilized copper（Ⅱ） catalyst （10 mol%） in methanol without any additives and bases. The reactions generated the corresponding cross-coupling products in good yields. Furthermore, silica-supported copper can be recovered and recycled by a simple filtration procedure and used for five consecutive trials without decreases in activity.
基金supported by the National Natural Science Foundation of China(21602096)。
文摘A simple electrochemically mediated method for the conversion of nitroarenes to aryl boronic esters is presented.Electrochemical borylation of a diverse range of nitroarenes,including the late-stage borylation of bioactive molecules,is furnished at room temperature under simple conditions,thereby demonstrating the broad utility and functional-group tolerance of this protocol.This transformation provides a convenient and practical access to aryl boronic esters from widely available nitroarenes,which would significantly streamline the synthetic process of diverse functionalized arenes.
基金We thank the National Key Research and Development Pro- gram （No. 2016YFA0202900}, the National Natural Science Foundation of China （No. 21772217）, Science and Technology Commis- sion of Shanghai Municipality （No. 18XD1405000）, the Strategic Priority Research Program of the Chinese Academy of Sciences （No. XDB20000000）, and Shanghai Institute of Organic Chemistry （sioczz201807） for financial support.
文摘The direct coupling of allylic alcohols with arylboronic acids or their derivatives catalyzed by Ni（cod）2 in the presence of a catalytic amount of base has been developed. A wide variety of allylic substrates or aryIboronic acids turned out to be applicable to this catalytic system. The present method does not require the use of ligands for stabilizing the nickel catalyst in most cases or additional activators for activation of altylic alcohols.
文摘The boron trifluoride induced Suzuki-Miyaura cross-coupling of aryltriazenes with arylboronic acids catalyzed by Pd（OAc）2 without added ligands has been achieved for the first time. The reactions performed at room temperature under an argon atmosphere give biaryls in good to excellent yields. It is noteworthy that the reactions were conducted under mild and ligand-free conditions.
基金We gratefully acknowledge the financial support of this work by the National Natural Science Foundation of China （No. 21563025）, Shihezi University Training Programme for Distinguished Youth Scholars （No. 2014ZRKXJQ05）, and Start-Up Foundation for Young Scientists of Shihezi University （RCZX201408）.
文摘Synthesis of triarylmethanes via metal-free reductive coupling of diaryl ketone, tosylhydrazide, and arylboronic acids has been developed. This methodology is realized via one-pot two-step reactions involving the preparation of N-tosylhydrazones by reacting tosylhydrazide with diaryl ketone derivatives, followed by the reductive coupling with arylboronic acid in the presence of potassium carbonate to afford various triarylmethanes analogues in moder- ate to good yields. Importantly, the system presented here enables the use of easily accessible starting materials and a series of substrates with diverse functional group could be tolerant in this reaction. This approach could also be particularly useful for the synthesis of triaryl-substituted carbazolyl compounds.
