Expedient Cobalt-Catalyzed C-H Alkynylation of (Enantiopure) Benzylamines

被引:60
作者
Landge, Vinod G. [1 ,3 ]
Midya, Siba P. [1 ,3 ]
Rana, Jagannath [1 ,3 ]
Shinde, Dinesh R. [2 ]
Balaraman, Ekambaram [1 ,3 ]
机构
[1] CSIR, Natl Chem Lab, Catalysis Div, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India
[2] CSIR, Natl Chem Lab, Cent NMR Facil, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India
[3] Acad Sci & Innovat Res, New Delhi 110025, India
关键词
TERMINAL ALKYNES; BOND ACTIVATION; DIRECTED FUNCTIONALIZATION; AMINOQUINOLINE BENZAMIDES; ORTHO-C(SP(2))-H BONDS; MECHANISTIC INSIGHTS; SELECTIVE ACCESS; CARBON-HYDROGEN; NICKEL; ANNULATION;
D O I
10.1021/acs.orglett.6b02549
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A unified strategy for cobalt-catalyzed ortho-C-H bond alkynylation of benzylamines is reported. Simple, commercially available CoBr2 was used as a cobalt source. The developed alkynylation strategy is robust and efficient and has a broad substrate scope including 1 degrees, 2 degrees, and 3 degrees benzylamines. The mechanistic study shows that C-H bond cleavage is reversible, and the kinetic study illustrates that the rate of reaction depends solely on the catalyst.
引用
收藏
页码:5252 / 5255
页数:4
相关论文
共 72 条
[1]   C-H ACTIVATION Following directions [J].
Ackermann, Lutz ;
Li, Jie .
NATURE CHEMISTRY, 2015, 7 (09) :686-687
[2]   Robust Ruthenium(II)-Catalyzed C-H Arylations: Carboxylate Assistance for the Efficient Synthesis of Angiotensin-II-Receptor Blockers [J].
Ackermann, Lutz .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2015, 19 (01) :260-269
[3]   Cobalt-Catalyzed C-H Arylations, Benzylations, and Alkylations with Organic Electrophiles and Beyond [J].
Ackermann, Lutz .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (19) :8948-8954
[4]   Ruthenium-Catalyzed Direct ortho-Alkynylation of Arenes with Chelation Assistance [J].
Ano, Yusuke ;
Tobisu, Mamoru ;
Chatani, Naoto .
SYNLETT, 2012, (19) :2763-2767
[5]   The medicinal chemist's toolbox for late stage functionalization of drug-like molecules [J].
Cernak, Tim ;
Dykstra, Kevin D. ;
Tyagarajan, Sriram ;
Vachal, Petr ;
Krska, Shane W. .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (03) :546-576
[6]   Cobalt-Catalyzed Coupling of Alkyl Grignard Reagent with Benzamide and 2-Phenylpyridine Derivatives through Directed C-H Bond Activation under Air [J].
Chen, Quan ;
Ilies, Laurean ;
Yoshikai, Naohiko ;
Nakamura, Eiichi .
ORGANIC LETTERS, 2011, 13 (12) :3232-3234
[7]   Cobalt-Catalyzed ortho-Alkylation of Secondary Benzamide with Alkyl Chloride through Directed C-H Bond Activation [J].
Chen, Quan ;
Ilies, Laurean ;
Nakamura, Eiichi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (03) :428-429
[8]   Bidentate, Monoanionic Auxiliary-Directed Functionalization of Carbon-Hydrogen Bonds [J].
Daugulis, Olafs ;
Roane, James ;
Tran, Ly Dieu .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (04) :1053-1064
[9]   Cobalt-catalyzed Branched-selective Addition of Aromatic Ketimines to Styrenes under Room-temperature Conditions [J].
Dong, Jinghua ;
Lee, Pin-Sheng ;
Yoshikai, Naohiko .
CHEMISTRY LETTERS, 2013, 42 (10) :1140-1142
[10]   Rhodium-Catalyzed C-H Alkynylation of Arenes at Room Temperature [J].
Feng, Chao ;
Loh, Teck-Peng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (10) :2722-2726