Cobalt-catalyze d re ductive alkynylation to construct C(sp)-C(sp3 ) and C(sp)-C(sp2 ) bonds

被引:15
作者
Wan, Lei [1 ]
Tong, Yizhou [1 ]
Lu, Xi [2 ]
Fu, Yao [1 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Res Ctr Phys Sci Microscale, CAS Key Lab Urban Pollutant Convers, Anhui Prov Key Lab Biomass Clean Energy,iChEM, Hefei 230026, Peoples R China
[2] Univ Sci & Technol China, Sch Chem & Mat Sci, Key Lab Precis & Intelligent Chem, Hefei 230026, Peoples R China
基金
美国国家科学基金会; 中国国家自然科学基金;
关键词
Cobalt; -catalysis; Cross-electrophile coupling; Carbon-carbon bond formation; Reductive alkynylation; Alkyne synthesis; SECONDARY ALKYL BROMIDES; CROSS-COUPLINGS; DECARBOXYLATIVE ALKYNYLATION; SONOGASHIRA REACTIONS; CARBOXYLIC-ACIDS; REACTIVITY; HALIDES;
D O I
10.1016/j.cclet.2023.109283
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Transition-metal-catalyzed cross-electrophile coupling has emerged as a reliable method for constructing carbon-carbon bonds. Herein, we report a general method, cobalt-catalyzed reductive alkynylation, to construct C(sp)-C(sp3 ) and C(sp)-C(sp2 ) bonds. This presented reaction has a broad substrate scope, enabling the efficient cross-electrophile coupling between alkynyl bromides with alkyl halides and aryl or alkenyl (pseudo)halides. This presented reaction is conducted under mild conditions, tolerating many functional groups, thus suitable for the modification and synthesis of biologically active molecules. (c) 2024 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
引用
收藏
页数:6
相关论文
共 78 条
[1]   Direct Method for Carbon-Carbon Bond Formation: The Functional Group Tolerant Cobalt-Catalyzed Alkylation of Aryl Halides [J].
Amatore, Muriel ;
Gosmini, Corinne .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (20) :5848-5852
[2]   Simple and efficient nickel-catalyzed cross-coupling reaction of alkynylalanes with benzylic and aryl bromides [J].
Biradar, Deepak B. ;
Gau, Han-Mou .
CHEMICAL COMMUNICATIONS, 2011, 47 (37) :10467-10469
[3]   Photo-induced copper-catalyzed alkynylation and amination of remote unactivated C(sp3)-H bonds [J].
Cao, Zhusong ;
Li, Jianye ;
Sun, Youwen ;
Zhang, Hanwen ;
Mo, Xueling ;
Cao, Xin ;
Zhang, Guozhu .
CHEMICAL SCIENCE, 2021, 12 (13) :4836-4840
[4]   Poly(o-xylylene)s via Cobalt-Catalyzed Reductive Polymerization [J].
Chen, Si ;
Zhao, Yanchuan .
CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (09) :952-958
[5]   Ni/AntPohs-Catalyzed Stereoselective Asymmetric Intramolecular Reductive Coupling of N-1,6-Alkynones [J].
Chen, Wanjun ;
Cheng, Yaping ;
Zhang, Tao ;
Mu, Yu ;
Jia, Wenqi ;
Liu, Guodu .
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (07) :5166-5182
[6]   Z-Selective Olefin Synthesis via Iron-Catalyzed Reductive Coupling of Alkyl Halides with Terminal Arylalkynes [J].
Cheung, Chi Wai ;
Zhurkin, Fedor E. ;
Hu, Xile .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (15) :4932-4935
[7]   Recent advances in Sonogashira reactions [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5084-5121
[8]   Cu(I)-Catalyzed Asymmetric Cross-Coupling of N-Tosylhydrazones and Trialkylsilylethynes: Enantioselective Construction of C(sp)C(sp3) Bonds [J].
Chu, Wen-Dao ;
Guo, Fangfang ;
Yu, Lefei ;
Hong, Junting ;
Liu, Qianyi ;
Mo, Fanyang ;
Zhang, Yan ;
Wang, Jianbo .
CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (03) :217-222
[9]   Cobalt-Catalyzed Cross-Coupling of Organozinc Halides with Bromoalkynes [J].
Corpet, Martin ;
Bai, Xian-Zhou ;
Gosmini, Corinne .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (14-15) :2937-2942
[10]   Selective Ni-catalyzed cross-electrophile coupling of alkynes, fluoroalkyl halides, and vinyl halides [J].
Dai, Yubei ;
Wang, Fang ;
Zhu, Shengqing ;
Chu, Lingling .
CHINESE CHEMICAL LETTERS, 2022, 33 (08) :4074-4078