Ni-Catalyzed C(sp2)-H alkylation of N-quinolylbenzamides using alkylsilyl peroxides as structurally diverse alkyl sources

被引：15

作者：

Tsuzuki, Saori ^{[1
]}

Sakurai, Shunya ^{[1
]}

Matsumoto, Akira ^{[2
]}

Kano, Taichi ^{[1
,3
]}

Maruoka, Keiji ^{[1
,2
,4
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan

[2] Kyoto Univ, Grad Sch Pharmaceut Sci, Kyoto 6068501, Japan

[3] Tokyo Univ Agr & Technol, Grad Sch Engn, Dept Appl Chem, Tokyo 1848588, Japan

[4] Guangdong Univ Technol, Sch Chem Engn & Light Ind, Guangzhou 510006, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2021年 / 57卷 / 64期

关键词：

C-H BONDS; AROMATIC AMIDES; METHYLATION; PROTODEBORONATION; FUNCTIONALIZATION; BENZAMIDES; BENZYLATION; GENERATION; ARYLATION; RADICALS;

D O I：

10.1039/d1cc02983e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Ni-catalyzed direct C-H alkylation of N-quinolylbenzamides using alkylsilyl peroxides as alkyl-radical precursors is described. The reaction forms a new C(sp(3))-C(sp(2)) bond via the selective cleavage of both C(sp(3))-C(sp(3)) and C(sp(2))-H bonds. This transformation shows a high functional-group tolerance and, due to the structural diversity of alkylsilyl peroxides, a wide range of alkyl chains including functional groups and complex structures can be introduced at the ortho-position of readily available N-quinolylbenzamide derivatives. Mechanistic studies suggest that the reaction involves a radical mechanism.

引用

页码：7942 / 7945

页数：4

共 55 条

[1] The Nickel(II)-Catalyzed Direct Benzylation, Allylation, Alkylation, and Methylation of C-H Bonds in Aromatic Amides Containing an 8-Aminoquinoline Moiety as the Directing Group
Aihara, Yoshinori
Wuelbern, Jendrik
Chatani, Naoto
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2015, 88 (03) : 438 - 446
[2] Ni(II)-Catalyzed Oxidative Coupling between C(sp2)-H in Benzamides and C(sp3)-H in Toluene Derivatives
Aihara, Yoshinori
Tobisu, Mamoru
Fukumoto, Yoshiya
Chatani, Naoto
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (44) : 15509 - 15512
[3] Nickel-Catalyzed Direct Alkylation of C-H Bonds in Benzamides and Acrylamides with Functionalized Alkyl Halides via Bidentate-Chelation Assistance
Aihara, Yoshinori
Chatani, Naoto
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) : 5308 - 5311
[4] Carboxylate Assisted Ni-Catalyzed CH Bond Allylation of Benzamides
Barsu, Nagaraju
Kalsi, Deepti
Sundararaju, Basker
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (26) : 9364 - 9368
[5] Nickel Catalysts/N,N′-Bidentate Directing Groups: An Excellent Partnership in Directed C-H Activation Reactions
Castro, Luis C. Misal
Chatani, Naoto
[J]. CHEMISTRY LETTERS, 2015, 44 (04) : 410 - 421
[6] The medicinal chemist's toolbox for late stage functionalization of drug-like molecules
Cernak, Tim
Dykstra, Kevin D.
Tyagarajan, Sriram
Vachal, Petr
Krska, Shane W.
[J]. CHEMICAL SOCIETY REVIEWS, 2016, 45 (03) : 546 - 576
[7] Nickel-catalyzed Suzuki Coupling of Cycloalkyl Silyl Peroxides with Boronic Acids
Chen, Lei
Yang, Jun-Cheng
Xu, Pengfei
Zhang, Jun-Jie
Duan, Xin-Hua
Guo, Li-Na
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (11) : 7515 - 7525
[8] Nickel-Catalyzed C-H Coupling with Allyl Phosphates: A Site-Selective Synthetic Route to Linear Allylarenes
Cong, Xuefeng
Li, Yuexuan
Wei, Yu
Zeng, Xiaoming
[J]. ORGANIC LETTERS, 2014, 16 (15) : 3926 - 3929
[9] Base-Catalyzed Aryl-B(OH)2 Protodeboronation Revisited: From Concerted Proton Transfer to Liberation of a Transient Aryl Anion
Cox, Paul A.
Reid, Marc
Leach, Andrew G.
Campbell, Andrew D.
King, Edward J.
Lloyd-Jones, Guy C.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (37) : 13156 - 13165
[10] Protodeboronation of Heteroaromatic, Vinyl, and Cyclopropyl Boronic Acids: pH-Rate Profiles, Autocatalysis, and Disproportionation
Cox, Paul A.
Leach, Andrew G.
Campbell, Andrew D.
Lloyd-Jones, Guy C.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (29) : 9145 - 9157

← 1 2 3 4 5 6 →