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

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 20期

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

页码：5252 / 5255

页数：4

共 50 条

[31] Cobalt-Catalyzed Oxidative C-H/C-H Cross-Coupling between Two Heteroarenes
Tan, Guangying
He, Shuang
Huang, Xiaolei
Liao, Xingrong
Cheng, Yangyang
You, Jingsong
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (35) : 10414 - 10418
[32] Cobalt-Catalyzed Alkynylation of Organic Compounds: Hydroalkynylation, Dehydrogenative Alkynylation, and Reductive Alkynylation
Ueda, Yohei
Tsurugi, Hayato
Mashima, Kazushi
SYNLETT, 2023, 34 (09) : 990 - 1000
[33] Cobalt-Catalyzed, Chelation-Assisted C-H Bond Functionalization
Yoshikai, Naohiko
SYNLETT, 2011, (08) : 1047 - 1051
[34] Cobalt-catalyzed C-H activation and regioselective intermolecular annulation with allenes
Li, Tianlei
Zhang, Chao
Tan, Yonghua
Pan, Weidong
Rao, Yu
ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (02): : 204 - 209
[35] Cobalt-Catalyzed Enantioselective C-H Carbonylation towards Chiral Isoindolinones
Teng, Ming-Ya
Wu, Yong-Jie
Chen, Jia-Hao
Huang, Fan-Rui
Liu, De-Yang
Yao, Qi-Jun
Shi, Bing-Feng
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (10)
[36] High-Valent Cobalt-Catalyzed C-H Bond Functionalization
Yoshino, Tatsuhiko
Matsunaga, Shigeki
ADVANCES IN ORGANOMETALLIC CHEMISTRY, VOL 68, 2017, 68 : 197 - 247
[37] Mechanochemical Cobalt-Catalyzed C-H Bond Functionalizations by Ball Milling
Cheng, Hanchao
Hernandez, Jose G.
Bolm, Carsten
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (09) : 1800 - 1804
[38] Cobalt-catalyzed C-H activation: recent progress in heterocyclic chemistry
Ujwaldev, Sankuviruthiyil M.
Harry, Nissy Ann
Divakar, Mathiyazhagan Arun
Anilkumar, Gopinathan
CATALYSIS SCIENCE & TECHNOLOGY, 2018, 8 (23) : 5983 - 6018
[39] Cobalt-Catalyzed Enantioselective Alkynylation of Oxabicyclic Alkenes
Wei, Lin-Wen
Ma, Zhan-Cai
Wang, Zhao-Qing
Zhao, Yu
Huang, Yuan
SYNTHESIS-STUTTGART, 2023, 55 (23): : 3954 - 3960
[40] Synthesis of Chiral Diarylmethylamines by Cobalt-Catalyzed Enantioselective C-H Alkoxylation
Wang, Zhen-Kai
Wu, Yong-Jie
Yao, Qi-Jun
Shi, Bing-Feng
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (28)

← 1 2 3 4 5 →