A nickel-catalyzed 1,1-diarylation of electronically unbiased alkenes has been developed,providing straightforward access to diarylalkanes from readily available materials.Importantly,both the efficiency and the regio...A nickel-catalyzed 1,1-diarylation of electronically unbiased alkenes has been developed,providing straightforward access to diarylalkanes from readily available materials.Importantly,both the efficiency and the regioselectivity of this transformation are ensured by reaction conditions,rather than the coordinating group of substrates.We also demonstrate that under balloon pressure,ethylene and propylene can also be utilized as substrates.Preliminary mechanistic experiments suggest that this transformation involves a Ni(0)/Ni(Ⅱ)catalytic cycle rather than a Ni(Ⅰ)/Ni(Ⅲ)cycle.展开更多
Triphenylphosphine and salicylaldimine could be used as a mixed ligand system to obtain a high catalytic activ- ity for palladium catalyzed diarylation of primary anilines with unactivated aryl chlorides by the synerg...Triphenylphosphine and salicylaldimine could be used as a mixed ligand system to obtain a high catalytic activ- ity for palladium catalyzed diarylation of primary anilines with unactivated aryl chlorides by the synergistic effect of ligands. The activity and selectivity of the catalytic system could be improved by modifying the structure of sa- licylaldimine. In refluxing o-xylene, PdC12（Ph3P）2 with 2,5-ditrifluoromethyl N-phenylsalicylaldimine as a coligand shows high efficiency for the diarylation of various anilines. The catalytic system shows good toleration for the ste- ric hindrance of the substrates. The facile catalytic system works as well on the multiple arylation of 1, 1＇-biphenyl- 4,4＇-diamine with aryl chlorides to afford N,N,N＇y＇-tetraaryl-1,1＇-biphenyl-4,4＇-diamines which are important in- termediates of organic light emitting diode （OLED） hole transport materials.展开更多
We report herein a palladium-catalyzed diarylative dearomatization of indole by employing thioester and arylboronic acid as the aryl electrophiles.The reaction involved a decarbonylation/migratory insertion/terminal S...We report herein a palladium-catalyzed diarylative dearomatization of indole by employing thioester and arylboronic acid as the aryl electrophiles.The reaction involved a decarbonylation/migratory insertion/terminal Suzuki coupling procedure.Substrates bearing various functional groups are well tolerated in the reaction,affording the diarylated indoline skeletons in moderate to good yields.展开更多
The Suzuki-Miyaura reaction of methyl-5-bromo-8-（tosyloxy）-1,6-naphthyridine-7-carboxylate（5）,with 2 equiv. of arylboronic acids gave diarylated product, 5,8–diaryl-1,6-naphthyridine-7-carboxylate（7）, whereas 1...The Suzuki-Miyaura reaction of methyl-5-bromo-8-（tosyloxy）-1,6-naphthyridine-7-carboxylate（5）,with 2 equiv. of arylboronic acids gave diarylated product, 5,8–diaryl-1,6-naphthyridine-7-carboxylate（7）, whereas 1 equiv. of arylboronic acid resulted in site-selective formation of 5-aryl-8-（tosyloxy）-1,6-naphthyridine-7-carboxylate（8）. The reactions proceeded with excellent chemo-selectivity in favor of the bromide group. Likewise, one-pot reaction with completely different boronic acids by sequential addition produced 1,6-naphthyridine-7-carboxylates,（10） containing two different aryl groups at 5 and 8 positions.展开更多
A new series of diaryl urea derivatives bearing N-acylhydrazone moiety were designed and synthesized. All the target compounds were evaluated for their antiproliferative activities against human leukemia cell line （H...A new series of diaryl urea derivatives bearing N-acylhydrazone moiety were designed and synthesized. All the target compounds were evaluated for their antiproliferative activities against human leukemia cell line （HL-60）, human lung adenocarcinoma epithelial cell line （A549） and human breast cancer cell line （MDA-MB-231） in vitro by standard MTT assay. The pharmacological results indicated that some compounds exhibited promising antitumor activities. Compound 1j showed the most potent antiproliferative activity against the tested three cell lines with IC50 values of 0.13 μmol/L, 0.7 μmol/L and 0.5μmol/L, respectively.展开更多
A series of novel diaryl ureas containing 4-[（2-amino-6-trifluromethyl）pyrimidine-4-yl]piperazine-l-yl group were synthesized and evaluated for their cytotoxic activities in a panel of human cancer cell lines. Compa...A series of novel diaryl ureas containing 4-[（2-amino-6-trifluromethyl）pyrimidine-4-yl]piperazine-l-yl group were synthesized and evaluated for their cytotoxic activities in a panel of human cancer cell lines. Compared with the reference drug Sorafenib,some compounds showed more potent and a broader spectrum of anti-cancer activities.Among them,compound 2p demonstrated significant inhibitory activities against MDA-MB-231,HT-29 and MCF-7 cell lines with IC_（50） values of 0.016,0.63,0.001μmol/L, respectively.展开更多
An efficient and simple protocol of copper-catalyzed C-S bond formation between aryl halides and inexpensive and commercially available aminothiourea is reported.A variety of symmetrical diaryl sulfides can be synthes...An efficient and simple protocol of copper-catalyzed C-S bond formation between aryl halides and inexpensive and commercially available aminothiourea is reported.A variety of symmetrical diaryl sulfides can be synthesized in good to excellent yields up to 94%with the advantage of avoiding foul-smelling thiols.展开更多
A new and ancient solid-state reaction using K3Fe(CN)(6)/KOII to oxidize diaryl semicarbazides for preparing azo compounds has been reported. Nine N-aryl-2-phenyl-diazenecarboxamides have been synthesized in excellent...A new and ancient solid-state reaction using K3Fe(CN)(6)/KOII to oxidize diaryl semicarbazides for preparing azo compounds has been reported. Nine N-aryl-2-phenyl-diazenecarboxamides have been synthesized in excellent yields with simple instrument.展开更多
A general synthesis of diaryl ethers via coupling of aryl halides with substituted phenoxytrimethylsilane in the presence of TBAF is described. The protocol is simple and mild, and gives good to excellent yields.
A rapid and efficient method for the preparation of diaryl thiourea compounds was reported for the first time. Twelve diaryl thiourea compounds that possessing biological activity have been synthesized in excellent yi...A rapid and efficient method for the preparation of diaryl thiourea compounds was reported for the first time. Twelve diaryl thiourea compounds that possessing biological activity have been synthesized in excellent yields (91-97%). The reaction proved to be extremely simple and highly efficient (in 1.5-4.5 min).展开更多
Nanoparticle Fe304 encapsulated CuO, as a heterogeneous catalyst, is a facile system for the synthesis of diaryl ethers by the cross-coupling reaction of various substituted aryl halides with various substituted pheno...Nanoparticle Fe304 encapsulated CuO, as a heterogeneous catalyst, is a facile system for the synthesis of diaryl ethers by the cross-coupling reaction of various substituted aryl halides with various substituted phenols, which avoids using any type of expensive ligand and can be recovered from the reaction mixture by using a simple magnet. Moreover, this catalyst can be reused three times with high catalytic activity.展开更多
Tetrabutylammonium fluoride （TBAF） effectively facilitated a denitrative substitution reaction of electron-deficient nitroarenes with phenylthiotrimethylsilane （PhSTMS） under mild and base-free neutral conditions ...Tetrabutylammonium fluoride （TBAF） effectively facilitated a denitrative substitution reaction of electron-deficient nitroarenes with phenylthiotrimethylsilane （PhSTMS） under mild and base-free neutral conditions at room temperature, providing a practical and efficient synthesis of useful unsymmetrical diaryl thioethers. Nitroarenes bearing ortho- and para-positioned electron-withdrawing groups are the most reactive substrates, indicating that this reaction most possibly proceeded via the nucleophilic aromatic substitution （SNAr） mechanism.展开更多
The non-toxic and magnetically separable nano-CuFeOcatalyzed synthesis of symmetrical aryl sulfides by the reaction of thiourea with a wide variety of aryl halides,including aryl chlorides has been reported.Excellent ...The non-toxic and magnetically separable nano-CuFeOcatalyzed synthesis of symmetrical aryl sulfides by the reaction of thiourea with a wide variety of aryl halides,including aryl chlorides has been reported.Excellent yields of products have been obtained under ligand-free conditions and without the use of any expensive catalyst,such as palladium.展开更多
Reduction of diaryldiselenides by the system of Cp2TiCl2/Bu'MgBr/THF gave the nucleophilic arylselenium complex. They reacted with diaryl iodonium salts to afford unsymmetrical diaryl selenides in high yields.
The diaryldiselenides reacted with titanocene hydried （Cp2TiH） generted from Cp2TiCl2/i-BuMgBr to give arylselenium complexes of titanocene. They reacted readily with diaryliodoiums salt to give unsymmetical diaryls...The diaryldiselenides reacted with titanocene hydried （Cp2TiH） generted from Cp2TiCl2/i-BuMgBr to give arylselenium complexes of titanocene. They reacted readily with diaryliodoiums salt to give unsymmetical diarylselenides.展开更多
A series of salicylaldimine ligands were designed to promote the copper-catalyzed Ullmann cross- coupling reaction. After a screening process, 2-（（2-isopropylphenylimino）methyl）phenol was found to serve as a good ...A series of salicylaldimine ligands were designed to promote the copper-catalyzed Ullmann cross- coupling reaction. After a screening process, 2-（（2-isopropylphenylimino）methyl）phenol was found to serve as a good supporting ligand for this reaction. Employing this Schiff-base ligand as a new supporting ligand, the copper-catalyzed coupling reactions of aryl bromides and aryl iodides with various phenols successfully proceeded in good yields under mild conditions. Various diaryl ethers were obtained with excellent yields in dioxane in the presence of K3P04 and a catalytic amount of copper（I） salt.展开更多
A series of 2-amino-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidinyl substituted diaryl urea derivatives was designed and synthesized. Their in vitro cytotoxicities against two cancer cell lines（Bel-7402 and A549） were ev...A series of 2-amino-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidinyl substituted diaryl urea derivatives was designed and synthesized. Their in vitro cytotoxicities against two cancer cell lines（Bel-7402 and A549） were evaluated by standard MTT assay. Six of tested compounds 6, 8, 10, 17, 21 and 22 exhibited more potent cytotoxicity superior to sorafenib. The structure activity relationship（SAR） study indicates that 2-amino-5,6,7,8-tetrahydropyrido- [4,3-d]pyrimidinyl group was an option for cytotoxic potency.展开更多
Seven diaryl ethers were synthesized with potassium fluoride coated alumina as a strong base and the addition of catalytic amount of PTC. The yield of diaryl ethers with addition of PTC was much higher than that witho...Seven diaryl ethers were synthesized with potassium fluoride coated alumina as a strong base and the addition of catalytic amount of PTC. The yield of diaryl ethers with addition of PTC was much higher than that without PTC.A discussion of the catalysis mechanism was given in this paper.展开更多
基金support from National Natural Science Foundation of China(21702151 and 21871211)the Fundamental Research Funds for Central Universities(2042019kf0208).
文摘A nickel-catalyzed 1,1-diarylation of electronically unbiased alkenes has been developed,providing straightforward access to diarylalkanes from readily available materials.Importantly,both the efficiency and the regioselectivity of this transformation are ensured by reaction conditions,rather than the coordinating group of substrates.We also demonstrate that under balloon pressure,ethylene and propylene can also be utilized as substrates.Preliminary mechanistic experiments suggest that this transformation involves a Ni(0)/Ni(Ⅱ)catalytic cycle rather than a Ni(Ⅰ)/Ni(Ⅲ)cycle.
基金We thank the National Natural Science Foundationof China （21272156） for financial support.
文摘Triphenylphosphine and salicylaldimine could be used as a mixed ligand system to obtain a high catalytic activ- ity for palladium catalyzed diarylation of primary anilines with unactivated aryl chlorides by the synergistic effect of ligands. The activity and selectivity of the catalytic system could be improved by modifying the structure of sa- licylaldimine. In refluxing o-xylene, PdC12（Ph3P）2 with 2,5-ditrifluoromethyl N-phenylsalicylaldimine as a coligand shows high efficiency for the diarylation of various anilines. The catalytic system shows good toleration for the ste- ric hindrance of the substrates. The facile catalytic system works as well on the multiple arylation of 1, 1＇-biphenyl- 4,4＇-diamine with aryl chlorides to afford N,N,N＇y＇-tetraaryl-1,1＇-biphenyl-4,4＇-diamines which are important in- termediates of organic light emitting diode （OLED） hole transport materials.
基金the Shanghai Institute of Materia Medicathe Chinese Academy of Sciences+4 种基金the National Natural Science Foundation of China(Nos.21772211 and 21920102003)the Youth Innovation Promotion Association CAS(Nos.2014229 and 2018293)the Science and Technology Commission of Shanghai Municipality(Nos.17JC1405000 and 18431907100)the Program of Shanghai Academic Research Leader(No.19XD1424600)the National Science&Technology Major Project“Key New Drug Creation and Manufacturing Program”,China(No.2018ZX09711002-006)for financial support。
文摘We report herein a palladium-catalyzed diarylative dearomatization of indole by employing thioester and arylboronic acid as the aryl electrophiles.The reaction involved a decarbonylation/migratory insertion/terminal Suzuki coupling procedure.Substrates bearing various functional groups are well tolerated in the reaction,affording the diarylated indoline skeletons in moderate to good yields.
基金the VIT University Vellore for the support and facilitiesSIF-VIT for their support of NMR(DST-FIST Fund)
文摘The Suzuki-Miyaura reaction of methyl-5-bromo-8-（tosyloxy）-1,6-naphthyridine-7-carboxylate（5）,with 2 equiv. of arylboronic acids gave diarylated product, 5,8–diaryl-1,6-naphthyridine-7-carboxylate（7）, whereas 1 equiv. of arylboronic acid resulted in site-selective formation of 5-aryl-8-（tosyloxy）-1,6-naphthyridine-7-carboxylate（8）. The reactions proceeded with excellent chemo-selectivity in favor of the bromide group. Likewise, one-pot reaction with completely different boronic acids by sequential addition produced 1,6-naphthyridine-7-carboxylates,（10） containing two different aryl groups at 5 and 8 positions.
基金supported by the National High Technology Research and Development Program (‘‘863’’ Program)of China (No. 2012AA020305)National Natural Science Foundation of China (No. 21002065)Shenyang Scienceand Technology Plan Projects (No. F11-151-9-00)
文摘A new series of diaryl urea derivatives bearing N-acylhydrazone moiety were designed and synthesized. All the target compounds were evaluated for their antiproliferative activities against human leukemia cell line （HL-60）, human lung adenocarcinoma epithelial cell line （A549） and human breast cancer cell line （MDA-MB-231） in vitro by standard MTT assay. The pharmacological results indicated that some compounds exhibited promising antitumor activities. Compound 1j showed the most potent antiproliferative activity against the tested three cell lines with IC50 values of 0.13 μmol/L, 0.7 μmol/L and 0.5μmol/L, respectively.
基金supported by a grant from the National Natural Science Foundation of China(No.21002065)
文摘A series of novel diaryl ureas containing 4-[（2-amino-6-trifluromethyl）pyrimidine-4-yl]piperazine-l-yl group were synthesized and evaluated for their cytotoxic activities in a panel of human cancer cell lines. Compared with the reference drug Sorafenib,some compounds showed more potent and a broader spectrum of anti-cancer activities.Among them,compound 2p demonstrated significant inhibitory activities against MDA-MB-231,HT-29 and MCF-7 cell lines with IC_（50） values of 0.016,0.63,0.001μmol/L, respectively.
基金supported by the Natural Science Foundation of Zhejiang Province(No.Y407240)
文摘An efficient and simple protocol of copper-catalyzed C-S bond formation between aryl halides and inexpensive and commercially available aminothiourea is reported.A variety of symmetrical diaryl sulfides can be synthesized in good to excellent yields up to 94%with the advantage of avoiding foul-smelling thiols.
基金the financial support from the Natural Science Foundation of Technology Commission of Henan Province.
文摘A new and ancient solid-state reaction using K3Fe(CN)(6)/KOII to oxidize diaryl semicarbazides for preparing azo compounds has been reported. Nine N-aryl-2-phenyl-diazenecarboxamides have been synthesized in excellent yields with simple instrument.
文摘A general synthesis of diaryl ethers via coupling of aryl halides with substituted phenoxytrimethylsilane in the presence of TBAF is described. The protocol is simple and mild, and gives good to excellent yields.
文摘A rapid and efficient method for the preparation of diaryl thiourea compounds was reported for the first time. Twelve diaryl thiourea compounds that possessing biological activity have been synthesized in excellent yields (91-97%). The reaction proved to be extremely simple and highly efficient (in 1.5-4.5 min).
基金supported by the Natural Science Foundation of Gansu Province,China(No.1014RJZA022)Postgraduate Tutor Fund of Gansu Province Education Department(No.1101ZTC103)
文摘Nanoparticle Fe304 encapsulated CuO, as a heterogeneous catalyst, is a facile system for the synthesis of diaryl ethers by the cross-coupling reaction of various substituted aryl halides with various substituted phenols, which avoids using any type of expensive ligand and can be recovered from the reaction mixture by using a simple magnet. Moreover, this catalyst can be reused three times with high catalytic activity.
基金the National Natural Science Foundation of China(No.20902070)Natural Science Foundation of Zhejiang Province(No.Y4100579)Qianjiang Talents Program of Zhejiang Province(No.QJD0902004) for financial supports
文摘Tetrabutylammonium fluoride （TBAF） effectively facilitated a denitrative substitution reaction of electron-deficient nitroarenes with phenylthiotrimethylsilane （PhSTMS） under mild and base-free neutral conditions at room temperature, providing a practical and efficient synthesis of useful unsymmetrical diaryl thioethers. Nitroarenes bearing ortho- and para-positioned electron-withdrawing groups are the most reactive substrates, indicating that this reaction most possibly proceeded via the nucleophilic aromatic substitution （SNAr） mechanism.
基金the funding support received for this project from the Isfahan University of Technology(1UT),IR Iran (A.R.H.) and Grant GM 33138(A.E.R.)the National Institutes of Health,USA.Further financial support from the Center of Excellency in Chemistry Research(IUT)
文摘The non-toxic and magnetically separable nano-CuFeOcatalyzed synthesis of symmetrical aryl sulfides by the reaction of thiourea with a wide variety of aryl halides,including aryl chlorides has been reported.Excellent yields of products have been obtained under ligand-free conditions and without the use of any expensive catalyst,such as palladium.
文摘Reduction of diaryldiselenides by the system of Cp2TiCl2/Bu'MgBr/THF gave the nucleophilic arylselenium complex. They reacted with diaryl iodonium salts to afford unsymmetrical diaryl selenides in high yields.
基金Project 29672008 was supported by NationalNatural Science Foundation of China.
文摘The diaryldiselenides reacted with titanocene hydried （Cp2TiH） generted from Cp2TiCl2/i-BuMgBr to give arylselenium complexes of titanocene. They reacted readily with diaryliodoiums salt to give unsymmetical diarylselenides.
基金the National Natural Science Foundation of ChinaKey Laboratory of Organic Synthesis of Jiangsu Province for the financial support(Nos.21201147,21302063,KJS1112)
文摘A series of salicylaldimine ligands were designed to promote the copper-catalyzed Ullmann cross- coupling reaction. After a screening process, 2-（（2-isopropylphenylimino）methyl）phenol was found to serve as a good supporting ligand for this reaction. Employing this Schiff-base ligand as a new supporting ligand, the copper-catalyzed coupling reactions of aryl bromides and aryl iodides with various phenols successfully proceeded in good yields under mild conditions. Various diaryl ethers were obtained with excellent yields in dioxane in the presence of K3P04 and a catalytic amount of copper（I） salt.
文摘A series of 2-amino-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidinyl substituted diaryl urea derivatives was designed and synthesized. Their in vitro cytotoxicities against two cancer cell lines（Bel-7402 and A549） were evaluated by standard MTT assay. Six of tested compounds 6, 8, 10, 17, 21 and 22 exhibited more potent cytotoxicity superior to sorafenib. The structure activity relationship（SAR） study indicates that 2-amino-5,6,7,8-tetrahydropyrido- [4,3-d]pyrimidinyl group was an option for cytotoxic potency.
文摘Seven diaryl ethers were synthesized with potassium fluoride coated alumina as a strong base and the addition of catalytic amount of PTC. The yield of diaryl ethers with addition of PTC was much higher than that without PTC.A discussion of the catalysis mechanism was given in this paper.
