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A simple and effective approach to the synthesis of alkynyl selenides from terminal alkynes 被引量:2
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作者 Barahman Movassagh Mozhgan Navidi 《Chinese Chemical Letters》 SCIE CAS CSCD 2012年第9期1035-1038,共4页
Alkynyl selenides were prepared under very mild conditions by reacting terminal alkynes with respective diorganic diselenides in the presence of potassium t-butoxide. The advantages of this protocol include the use of... Alkynyl selenides were prepared under very mild conditions by reacting terminal alkynes with respective diorganic diselenides in the presence of potassium t-butoxide. The advantages of this protocol include the use of readily available substrates and reagent and good yield of the products. 展开更多
关键词 Alkynyl selenides Diorganie diselenides Potassium t-butoxide terminal alkynes Phenyl acetylene
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Tri(t-butyl)phosphine-assisted selective hydrosilylation of terminal alkynes 被引量:1
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作者 Wu, Wei Zhang, Xiao Yun +1 位作者 Kang, Shou Xing Gao, Yan Min 《Chinese Chemical Letters》 SCIE CAS CSCD 2010年第3期312-316,共5页
A highly efficient and regio-/stereoselective method of hydrosilylating terminal alkynes was developed using Pt(DVDS)-tri(t-butyl) phosphine catalyst system at room temperature.Trans-products or alpha-products were ob... A highly efficient and regio-/stereoselective method of hydrosilylating terminal alkynes was developed using Pt(DVDS)-tri(t-butyl) phosphine catalyst system at room temperature.Trans-products or alpha-products were obtained almost exclusively depending on the alkynes and silanes employed. 展开更多
关键词 HYDROSILYLATION terminal alkynes Tri(t-butyl)phosphine PLATINUM
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On-surface construction of low-dimensional nanostructures with terminal alkynes: Linking strategies and controlling methodologies
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作者 Jing Liu Qi-Wei Chen Kai Wu 《Chinese Chemical Letters》 SCIE CAS CSCD 2017年第8期1631-1639,共9页
Bottom-up approach to constructing low-dimensional nanostructures on surfaces with terminal alkynes has drawn great interest because of its potential applications in fabricating advanced functional nanomaterials. The ... Bottom-up approach to constructing low-dimensional nanostructures on surfaces with terminal alkynes has drawn great interest because of its potential applications in fabricating advanced functional nanomaterials. The diversity of the achieved products manifests rich chemistry of terminal alkynes and hence careful linking strategies and proper controlling methodologies are required for selective preparations of high-quality target nanoarchitectures. This review summarizes various on-surface linking strategies for terminal alkynes, including non-bonding interactions as well as organometallic and covalent bonds, and presents examples to show effective control of surface assemblies and reactions of terminal alkynes by variations of the precursor structures, substrates and activation modes. Systematic studies of the on-surface linkage of terminal alkynes may help efficient and predictable preparations of surface nanomaterials and further understanding of surface chemistry. 展开更多
关键词 terminal alkynes On-surface reactions Surface assemblies Scanning tunneling microscopy Low-dimensional nanostructures
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Catalytic nucleophilic addition of terminal alkynes to α,β-unsaturated-γ-lactams
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作者 王茂荣 高宝 黄汉民 《Chinese Journal of Catalysis》 SCIE EI CAS CSCD 北大核心 2016年第4期476-483,共8页
A novel catalytic reaction has been developed for the nucleophilic addition of terminal alkynes toα,β‐unsaturated‐γ‐lactams via a cyclic N‐acyliminium ion intermediate. This simple reaction pro‐ceeds rapidly u... A novel catalytic reaction has been developed for the nucleophilic addition of terminal alkynes toα,β‐unsaturated‐γ‐lactams via a cyclic N‐acyliminium ion intermediate. This simple reaction pro‐ceeds rapidly under mild conditions, and provided a practical approach for the synthesis of a wide range of 5‐alkynyl‐2‐pyrrolidinones in moderate to good yields (45%–76%). 展开更多
关键词 Carbon-hydrogen addition Bronsted acid N-Acyliminium ion terminal alkyne Pyrrolidin-2-one
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Hydroarylation of terminal alkynes with arylboronic acids catalyzed by low loadings of palladium
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作者 Lei Xu Shiyu Li +3 位作者 Qi Zhang Ning Deng Biao Zhang Huajian Xu 《Chinese Chemical Letters》 SCIE CAS CSCD 2023年第2期165-169,共5页
The hydroarylation reaction of terminal alkynes with arylboronic acids catalyzed by low(400 ppm) loadings of palladium has been developed. The reaction is broad in scope and high-yielding, even on multigram scale. It ... The hydroarylation reaction of terminal alkynes with arylboronic acids catalyzed by low(400 ppm) loadings of palladium has been developed. The reaction is broad in scope and high-yielding, even on multigram scale. It is suitable for the synthesis of alkenes labeled with deuterium, and for the late-stage modification of bioactive molecules. 展开更多
关键词 HYDROARYLATION Low loadings terminal alkyne Deuterium-labeled PALLADIUM
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Higher Order Cuprate Species( Ⅱ )——Stereospecific Carbocupration of Terminal Alkynes and Its Synthetic Utility for ( ± )-Ipsenol and (E)-β-Farnesene
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作者 PAN Yi-jun , XU Zhang-huang, CHEN Jia-wei SUN Dong-chen (Department of Chemistry, Hubei University, Wuhan, 430062) To whom correspondence should be addressed. 《Chemical Research in Chinese Universities》 SCIE CAS CSCD 1993年第2期104-109,共6页
The stereospecific carbocupration of terminal alkynes via higher order cuprates to give 1,1'-disubstituted olefins with 99% configuration purity is described. Its synthetic utility as a general method for the prep... The stereospecific carbocupration of terminal alkynes via higher order cuprates to give 1,1'-disubstituted olefins with 99% configuration purity is described. Its synthetic utility as a general method for the preparation of substituted olefins is further illustrated by the direct synthesis of (±)-ipsenol and (E)-β-farnesene with highly geometric purity of the carbon-carbon double bond. 展开更多
关键词 Higher order cuprate terminal alkyne Carbocupration STEREOSPECIFIC
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Chiral bis(imidazoline)NCN pincer iridium(III)-catalyzed enantioselective alkynylation of trifluoropyruvates with terminal alkynes
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作者 Xiao-Qi Zhang Hui-Jie Wang +2 位作者 Hui Jiang Mao-Ping Song Jun-Fang Gong 《Green Synthesis and Catalysis》 2025年第4期429-434,共6页
Readily prepared chiral bis(imidazoline)NCN pincer iridium(III)complexes have been developed as the new and highly stereoselective catalysts for the direct asymmetric addition of terminal alkynes to trifluoropyruvates... Readily prepared chiral bis(imidazoline)NCN pincer iridium(III)complexes have been developed as the new and highly stereoselective catalysts for the direct asymmetric addition of terminal alkynes to trifluoropyruvates.With a catalyst loading of 5 mol%,a variety of optically activeα-trifluoromethylated tertiary propargylic alcohols were thus produced in good yields with high enantioselectivity(27 examples,74%–96%ee).Both enantiomers of the catalysis products were obtained by using enantiomeric Ir(III)catalysts.In addition,gram scale synthesis of the product and its transformation to a potentially very useful 2H-1,2,3-triazole compound were accomplished.Control experiments suggested that the alkynylide Ir(III)intermediates were involved in the reactions. 展开更多
关键词 Asymmetric alkynylation Pincer iridium(III)catalyst TRIFLUOROPYRUVATE terminal alkyne Alkynylide iridium(III)intermediate Chiral 2H-1 2 3-triazole
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Cobalt-catalyzed highly α-selective hydrostannylation of terminal alkynes
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作者 Yufeng Sun Bingcheng Wang +4 位作者 Cheng Wang Jiajing Li Jieping Chen Xin Hong Zhan Lu 《Science China Chemistry》 2025年第6期2491-2499,共9页
Transition metal-catalyzed hydrostannylation of alkynes is an atom-economic way towards valuableα-vinylstannanes.However,directing-group-free examples for the construction ofα-adducts are rare and mostly undergo the... Transition metal-catalyzed hydrostannylation of alkynes is an atom-economic way towards valuableα-vinylstannanes.However,directing-group-free examples for the construction ofα-adducts are rare and mostly undergo the M-Sn species insertion process.Here,we report an efficient cobalt-catalyzed highlyα-selective hydrostannylation of terminal alkynes via M-H species,using readily available Bu3Sn H and easily accessible as well as bench-stable ligand.The robust catalytic system,bearing good functional group tolerance and operational simplicity,provides theα-vinylstannanes in moderate to excellent yields with≥97:3 rr averagely.The efficiency of the reaction is investigated with turnover number(TON)up to 10,000 and turnover frequency(TOF)up to 144,000 h^(-1),respectively.The synthetic utility of theα-vinylstannanes is proved by further derivatizations towards the 1,1-disubstituted alkenes via Kosugi-Migita-Stille cross-coupling,conjugated alkene,α-vinyliodine,α-vinylazide,and allyl alcohol.Several control experiments,deuterium-labeling experiment and density functional theory(DFT)calculations are conducted to reveal the preliminary mechanism. 展开更多
关键词 HYDROSTANNYLATION cobalt-catalyzed α-selective terminal alkyne
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Iron-mediated cross dehydrogenative coupling(CDC) of terminal alkynes with benzylic ethers and alkanes 被引量:6
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作者 XIANG Shi-Kai ZHANG Bo +2 位作者 ZHANG Li-He CUI YuXin JIAO Ning 《Science China Chemistry》 SCIE EI CAS 2012年第1期50-54,共5页
Iron-mediated sp-sp3 C-C bond formation through the cross dehydrogenative coupling(CDC) of terminal alkynes with benzylic ethers or alkanes has been developed.The inexpensive iron salt is used as the catalyst to make ... Iron-mediated sp-sp3 C-C bond formation through the cross dehydrogenative coupling(CDC) of terminal alkynes with benzylic ethers or alkanes has been developed.The inexpensive iron salt is used as the catalyst to make this transformation environmentally benign.Iron-mediated sp-sp3 C-C bond formation through the cross dehydrogenative coupling(CDC) of terminal alkynes with benzylic ethers or alkanes has been developed.The inexpensive iron salt is used as the catalyst to make this transformation environmentally benign. 展开更多
关键词 IRON cross dehydrogenative coupling terminal alkynes benzylic ethers
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Specific cross-dimerization of terminal alkynes via Pd/TMEDA catalysis 被引量:1
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作者 Lixin Liu Jianyu Dong +5 位作者 Zuqi Fu Lebin Su Shaofeng Wu Qian Shang Shuang-Feng Yin Yongbo Zhou 《Science China Chemistry》 SCIE EI CAS CSCD 2022年第12期2487-2493,共7页
The cross-dimerization of terminal alkynes is the most straightforward and attractive approach to differently substituted 1,3-enynes,which are vital structural motifs in natural products,biologically active compounds,... The cross-dimerization of terminal alkynes is the most straightforward and attractive approach to differently substituted 1,3-enynes,which are vital structural motifs in natural products,biologically active compounds,and organic functional materials,etc.However,due to the inherent issues of the stereo-,regio-,and chemoselectivity,the strategy is less explored and remains problematic in substrate scope,selectivity,and screening of catalytic system,etc.Herein,a specific cross-dimerization of terminal alkynes is developed under Pd/TMEDA catalysis,which produces a series of gem-1,3-enynes(58 examples)in totally moderate to high yields with outstanding functional group tolerance.A cyclopalladium compound might be the key imtermediate,which performs anti-addition-carbometallation,and leads to the exclusive cross-selectivity.The unprecedented features of the reaction,such as anti-addition-carbometallation,easy control of selectivity,wide range of the donor alkynes,and very simple catalytic conditions,allow it not only a facile and functionally diverse synthesis of 1,3-enynes,but also a substantial progress for the textbook reaction. 展开更多
关键词 cross-dimerization Pd/TMEDA catalysis terminal alkynes gem-1 3-enynes
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Engineering Cu_(2)O/Cu/N-C interface to induce directional migration of charge for driving photocatalytic homo-coupling of terminal alkynes
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作者 Xiaoqin Yan Tianyi Xu +8 位作者 Wenwen Zhan Yang Yang Yang Yu Jianjian Yi Xiaoxiao He Lei Yang Jianwei Zhao Liming Sun Xiguang Han 《Nano Research》 SCIE EI CSCD 2024年第8期6895-6902,共8页
The efficient utilization of visible light catalysts for organic reactions necessitates not only the effective separation of photogenerated electrons and holes to participate in the reaction,but also their ability to ... The efficient utilization of visible light catalysts for organic reactions necessitates not only the effective separation of photogenerated electrons and holes to participate in the reaction,but also their ability to form key intermediates with reactant molecules.The present study successfully synthesized a crusiform-like mesoporous structure of nitrogen-doped carbon-coated Cu_(2)O/Cu(Cu_(2)O/Cu/N-C)with a Cu_(2)O/dual electron acceptor interface using etched HKUST-1 as the precursor.A series of theoretical and experimental studies have demonstrated that the Cu_(2)O/Cu/N-C interface in the photocatalytic homo-coupling of terminal alkynes not only effectively enhances the separation of photogenerated electron−hole pairs,but also facilitates the formation of the key intermediate[Cu_(2)O/Cu/N-C]-phenylacetylide and promotes the rearrangement of its internal charges.As a result,the homo-coupling reaction can be effectively facilitated.The primary reason for the functional role of Cu_(2)O/Cu/N-C interface lies in the downward bending of energy band from Cu_(2)O to N-doped C layers,induced by the different work functions of Cu_(2)O,Cu and N-doped C layers.Consequently,Cu_(2)O/Cu/N-C photocatalysts demonstrate exceptional photocatalytic activity in the homo-coupling reaction of terminal alkynes under blue-light irradiation and air atmosphere.The present study presents a novel research methodology for the development of highly efficient visible light catalysts to facilitate organic reactions in future applications. 展开更多
关键词 photocatalysis homo-coupling of terminal alkynes directional migration of charges heterojunction interface Cu_(2)O carbon coated
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Rhodium/Ming-Phos-catalyzed asymmetric annulation reaction of silacyclobutanes with terminal alkynes
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作者 Yue Sun Kaida Zhou +2 位作者 Chun Ma Zhiming Li Junliang Zhang 《Green Synthesis and Catalysis》 2024年第3期205-210,共6页
Asymmetric ring-expansion reactions of silacyclobutanes(SCBs)with alkynes have evolved as one of the powerful protocols for the construction of silicon-stereogenic compounds.However,the achievement of highly enantiose... Asymmetric ring-expansion reactions of silacyclobutanes(SCBs)with alkynes have evolved as one of the powerful protocols for the construction of silicon-stereogenic compounds.However,the achievement of highly enantioselective annulation of SCBs with terminal alkynes remains a challenge.Herein,we report a rhodium-catalyzed asymmetric annulation reaction of SCBs with terminal alkynes,which relies on the newly identified chiral sulfinamide phosphine ligand Ming-Phos.This catalytic system exhibits unique effects under mild conditions,leading to the direct synthesis of structurally diverse chiral silacycles in moderate to good yields with high enantioselectivities(up to 95%ee). 展开更多
关键词 Rhodium-catalysis Asymmetric annulation reaction Silicon-stereogenic Silacyclobutanes terminal alkynes
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Mercurous Chloride Catalyzed Mannich Condensation of Terminal Alkynes with Secondary Amines and Aldehydes 被引量:1
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作者 李品华 王磊 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2005年第8期1076-1080,共5页
Mercurous chloride catalyzed Mannich condensation of terminal alkynes with secondary amines and aldehydes has been developed. The reaction generated β-aminoalkynes in good yields.
关键词 Mannich reaction terminal alkyne secondary amine ALDEHYDE β-aminoalkyne mercurous chloride
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Studies on sulfinatodehalogenation XVI.Sodium dithionite-initiated addition of perfluoroalkyl iodides to terminal alkynes
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作者 HUANG, Wei-Yuan LU, Long ZHANG, Yuan-Fa Shanghai Institute of Organic Chemistry, Academia Sinica, Shanghai 200032 《Chinese Journal of Chemistry》 SCIE CAS CSCD 1990年第4期350-354,共10页
Reaction of perfluoroalkyl iodides with a series of alkynes under sulfinatodehalogenation condition gave a mixture of E/Z adducts very readily in high yield, thus constituted a mild, convenient and effective new metho... Reaction of perfluoroalkyl iodides with a series of alkynes under sulfinatodehalogenation condition gave a mixture of E/Z adducts very readily in high yield, thus constituted a mild, convenient and effective new method for the addition of perfluoroalkyl iodides to alkynes. Under the same con- dition, in the presence of 1-hexyne perfluoroalkyl bromide and 1,1,1-trichlorotrifluoroethane reacted only to give sulfinates as the major products. A radical mechanism was proposed for the addition reaction. 展开更多
关键词 SF Studies on sulfinatodehalogenation XVI.Sodium dithionite-initiated addition of perfluoroalkyl iodides to terminal alkynes
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Platinum-Catalyzed Asymmetric Ring-opening Reaction of Oxabenzonorbornadiene with Terminal Alkynes 被引量:1
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作者 Yuhua Long Han Jiang +2 位作者 Zhifu Zou Kaixuan Chen Yali Fang 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2014年第7期613-618,共6页
A novel platinum-catalyzed asymmetric ring-opening reaction of oxabenzonorbornadiene with terminal alkynes is described.The reaction affords optically active cis-2-alkynyl-1,2-dihydronaphthalen-1-ols in moderate yield... A novel platinum-catalyzed asymmetric ring-opening reaction of oxabenzonorbornadiene with terminal alkynes is described.The reaction affords optically active cis-2-alkynyl-1,2-dihydronaphthalen-1-ols in moderate yields with good enantioselectivity in the presence of catalytic amounts of Pt(COD)Cl_(2)/(S)-BINAP and an excess of zinc powder.The products were obtained exclusively with the relative cis-configuration of the ring substituents and the prevalent(1R,2S)-configuration of the stereocenters,as determined by single crystal X-ray diffraction analysis. 展开更多
关键词 platinum-catalyzed asymmetric catalysis ring-opening reaction oxabenzonorbornadiene terminal alkyne
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Syntheses of N-sulfonyl-N,N-disubstituted amidines via a three-component free-radical coupling reaction of tertiary amines and arenesulfonyl azides with terminal alkynes 被引量:1
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作者 HE XinWei SHANG YongJia +3 位作者 HU JinSong JU Kai JIANG Wei WANG SuFang 《Science China Chemistry》 SCIE EI CAS 2012年第2期214-222,共9页
A facile and efficient synthesis of N-sulfonyl-N,N-disubstituted amidines has been achieved via a CuI-catalyzed three-component free-radical coupling reaction of tertiary amines and arenesulfonyl azides with terminal ... A facile and efficient synthesis of N-sulfonyl-N,N-disubstituted amidines has been achieved via a CuI-catalyzed three-component free-radical coupling reaction of tertiary amines and arenesulfonyl azides with terminal alkynes in the presence of azodiisobutyronitrile(AIBN).The reaction mechanism of this reaction has also been studied. 展开更多
关键词 free radical multicomponent reaction sulfonyl azide terminal alkyne
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Microwave-enhanced Mannich Condensation of Terminal Alkynes, Primary Amines with Paraformaldehyde on Cuprous Iodide Doped Alumina under Solvent Free Conditions
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作者 王磊 李品华 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2003年第6期710-713,共4页
A microwave enhanced, solventless Mannich condensation of terminal alkynes, primary amines with paraformaldehyde on cuprous iodide doped alumina has been investigated. The structures of products depend on the ratio o... A microwave enhanced, solventless Mannich condensation of terminal alkynes, primary amines with paraformaldehyde on cuprous iodide doped alumina has been investigated. The structures of products depend on the ratio of alkyne to amine and paraformaldehyde. 展开更多
关键词 Mannich condensation terminal alkyne para^form^aldehyde primary amine cuprous iodide ALUMINA solvent free microwave irradiation
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FeCl_(3-) and GaCl_(3-) Catalyzed Dehydrative Coupling Reaction of Chromone-Derived Morita-Baylis-Hillman Alcohols with Terminal Alkynes
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作者 武陈 曾皓 +3 位作者 刘哲 刘利 王东 陈拥军 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2011年第12期2732-2738,共7页
FeCl3- and GaCl3-catalyzed dehydrative coupling reactions of chromone-derived Morita-Baylis-Hillman (MBH) alcohols with terminal alkynes were developed. The reactions provided exclusively a-regioselective and acetyl... FeCl3- and GaCl3-catalyzed dehydrative coupling reactions of chromone-derived Morita-Baylis-Hillman (MBH) alcohols with terminal alkynes were developed. The reactions provided exclusively a-regioselective and acetylene-substituted products in good yields. 展开更多
关键词 Morita-Baylis-Hillman alcohol CHROMONE FeCl3 GaCl3 terminal alkyne dehydrative coupling
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Synthesis of Unsymmetrical 1,3-Diynes via Pd/Cu-Catalyzed Cross-Coupling of Terminal Alkynes at Room Temperature
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作者 Yashuai Liu Ping Liu +3 位作者 Ningning Gu Jianwei Xie Yan Liu Bin Dai 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2016年第9期895-900,共6页
A facile and practical synthetic route of unsymmetrical 1,3-diynes via the PdC1/CuI catalyzed oxidative coupling of two different terminal alkynes has been developed by using 3-(diphenylphosphino)propanoic acid as a... A facile and practical synthetic route of unsymmetrical 1,3-diynes via the PdC1/CuI catalyzed oxidative coupling of two different terminal alkynes has been developed by using 3-(diphenylphosphino)propanoic acid as a ligand in the presence of oxygen. This system is suitable for not only aromatic alkynes but also heteroaromatic and aliphatic alkynes which were transformed into the corresponding unsymmetrical 1,3-diynes in moderate to good yields at room temperature. Moreover, the unsymmetrical 1,3-diynes were also obtained on a multi-gram scale. Mechanistic studies suggest that oxygen plays a key role in the catalytic cycles. 展开更多
关键词 unsymmetrical 1 3-diynes PALLADIUM P O ligand terminal alkyne CROSS-COUPLING
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Organic Polyvalent Iodinc Reagents-Promoted Coupling Reaction of 1-Alkynes
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作者 Jun Hua WANG Xian HUANG(Department of Chemistry. Zhejiang University Campus Xixi . Hangzhou 310028) 《Chinese Chemical Letters》 SCIE CAS CSCD 1999年第7期529-530,共2页
Teminal alkynes couple smoothly in the presence of PhI(OAc)2 or PhI(OH)OTs.catalytie Cul and base. affording conjugated diynes.
关键词 terminal alkynes coupling organic polyvalent iodine compounds conjugated diynes
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