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

[1] Cobalt-Catalyzed Bis-alkynylation of Amides via Double C-H Bond Activation
Landge, Vinod G.
Jaiswal, Garima
Balaraman, Ekambaram
ORGANIC LETTERS, 2016, 18 (04) : 812 - 815
[2] Manganese-Catalyzed C-H Alkynylation: Expedient Peptide Synthesis and Modification
Ruan, Zhixiong
Sauermann, Nicolas
Manoni, Elisabetta
Ackermann, Lutz
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (12) : 3172 - 3176
[3] Cobalt-Catalyzed Oxidative C-H Activation: Strategies and Concepts
Mei, Ruhuai
Dhawa, Uttam
Samanta, Ramesh C.
Ma, Wenbo
Wencel-Delord, Joanna
Ackermann, Lutz
CHEMSUSCHEM, 2020, 13 (13) : 3306 - 3356
[4] Cobalt-Catalyzed Tandem C-H Activation/C-C Cleavage/C-H Cyclization of Aromatic Amides with Alkylidenecyclopropanes
Li, Mingliang
Kwong, Fuk Yee
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (22) : 6512 - 6516
[5] Cobalt-Catalyzed Enantioselective C-H Annulation with Alkenes
Yang, Dandan
Zhang, Xian
Wang, Xinghua
Si, Xiao-Ju
Wang, Jingtao
Wei, Donghui
Song, Mao-Ping
Niu, Jun-Long
ACS CATALYSIS, 2023, 13 (07): : 4250 - 4260
[6] High-Valent Cobalt-Catalyzed C-H Bond Functionalization
Yoshino, Tatsuhiko
Matsunaga, Shigeki
ADVANCES IN ORGANOMETALLIC CHEMISTRY, VOL 68, 2017, 68 : 197 - 247
[7] 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
[8] Electrochemical Cobalt-Catalyzed C-H Activation
Sauermann, Nicolas
Meyer, Tjark H.
Ackermann, Lutz
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (61) : 16209 - 16217
[9] Cobalt-catalyzed C-H olefination of aromatics with unactivated alkenes
Manoharan, Ramasamy
Sivakumar, Ganesan
Jeganmohan, Masilamani
CHEMICAL COMMUNICATIONS, 2016, 52 (69) : 10533 - 10536
[10] Electrochemical Cobalt-Catalyzed C-H Oxygenation at Room Temperature
Sauermann, Nicolas
Meyer, Tjark H.
Tian, Cong
Ackermann, Lutz
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (51) : 18452 - 18455

← 1 2 3 4 5 →