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 72 条

[31] Oxidative Coupling between Two Hydrocarbons: An Update of Recent C-H Functionalizations [J].

Liu, Chao ;

Yuan, Jiwen ;

Gao, Meng ;

Tang, Shan ;

Li, Wu ;

Shi, Renyi ;

Lei, Aiwen .

CHEMICAL REVIEWS, 2015, 115 (22) :12138-12204

[32] Manganese-Catalyzed C-H Activation [J].

Liu, Weiping ;

Ackermann, Lutz .

ACS CATALYSIS, 2016, 6 (06) :3743-3752

[33] Ni(II)-catalyzed dehydrative alkynylation of unactivated (hetero) aryl C-H bonds using oxygen: a user-friendly approach [J].

Liu, Yan-Hua ;

Liu, Yue-Jin ;

Yan, Sheng-Yi ;

Shi, Bing-Feng .

CHEMICAL COMMUNICATIONS, 2015, 51 (58) :11650-11653

[34] A sustainable and simple catalytic system for direct alkynylation of C(sp2)-H bonds with low nickel loadings [J].

Liu, Yue-Jin ;

Liu, Yan-Hua ;

Yan, Sheng-Yi ;

Shi, Bing-Feng .

CHEMICAL COMMUNICATIONS, 2015, 51 (29) :6388-6391

[35] Copper/Silver-Mediated Direct ortho-Ethynylation of Unactivated (Hetero) aryl C-H Bonds with Terminal Alkyne [J].

Liu, Yue-Jin ;

Liu, Yan-Hua ;

Yin, Xue-Song ;

Gu, Wen-Jia ;

Shi, Bing-Feng .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (01) :205-209

[36] Cobalt(II)-Catalyzed Oxidative C-H Alkenylations: Regio- and Site-Selective Access to Isoindolin-1-one [J].

Ma, Wenbo ;

Ackermann, Lutz .

ACS CATALYSIS, 2015, 5 (05) :2822-2825

[37] Nickel- and Copper-Catalyzed Direct Alkynylation of Azoles and Polyfluoroarenes with Terminal Alkynes under O2 or Atmospheric Conditions [J].

Matsuyama, Naoto ;

Kitahara, Masanori ;

Hirano, Koji ;

Satoh, Tetsuya ;

Miura, Masahiro .

ORGANIC LETTERS, 2010, 12 (10) :2358-2361

[38] Cobalt-Catalyzed Oxidase C-H/N-H Alkyne Annulation: Mechanistic Insights and Access to Anticancer Agents [J].

Mei, Ruhuai ;

Wang, Hui ;

Warratz, Svenja ;

Macgregor, Stuart A. ;

Ackermann, Lutz .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (20) :6759-6763

[39] Cobalt-Catalyzed C-H Activation [J].

Moselage, Marc ;

Li, Jie ;

Ackermann, Lutz .

ACS CATALYSIS, 2016, 6 (02) :498-525

[40] Low-Valent Iron-Catalyzed C-C Bond Formation-Addition, Substitution, and C-H Bond Activation [J].

Nakamura, Eiichi ;

Yoshikai, Naohiko .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (18) :6061-6067

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