Nickel-catalyzed N-arylation of amines with arylboronic acids under open air

被引：17

作者：

Ando, Shin ^{[1
]}

Hirota, Yurina ^{[1
]}

Matsunaga, Hirofumi ^{[1
]}

Ishizuka, Tadao ^{[1
]}

机构：

[1] Kumamoto Univ, Fac Life Sci, Chuo Ku, 5-1 Oe Honmachi, Kumamoto 8620973, Japan

来源：

TETRAHEDRON LETTERS | 2019年 / 60卷 / 18期

关键词：

NHC; Nickel catalyst; Chan-Lam; C-N coupling; DYNAMIC KINETIC RESOLUTION; HETEROATOM BOND FORMATION; CROSS-COUPLING REACTIONS; C-N; ARYL; COMPLEXES; ETHERS; LIGAND; ESTERS; TRANSMETALATION;

D O I：

10.1016/j.tetlet.2019.04.004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this study, a well-defined, novel NHC-Ni complex was developed and used to catalyze the N-arylation of alkyl- and arylamines with arylboronic acids in a rare version of Chan-Lam coupling. Although the same coupling using copper catalysts has been widely studied, the nickel-catalyzed version is rare and normally requires 10-20 mol% catalyst loading. This novel NHC-Ni complex in combination with 4,4'-dimethyl-2,2'-bipyridine, however, proved to be an effective catalyst that lowered the required catalyst loading to only 2.0 mol%. (C) 2019 Elsevier Ltd. All rights reserved.

引用

页码：1277 / 1280

页数：4

共 51 条

[1] Reaction of nickelocene with 1,3-dimesitylimidazolium chloride
Abernethy, CD
Cowley, AH
Jones, RA
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 596 (1-2) : 3 - 5
[2] An N-Heterocyclic Carbene-Nickel Half-Sandwich Complex as a Precatalyst for Suzuki Miyaura Coupling of Aryl/Heteroaryl Halides with Aryl/Heteroarylboronic Acids
Ando, Shin
Matsunaga, Hirofumi
Ishizuka, Tadao
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (02) : 1266 - 1272
[3] C-N bond forming cross-coupling reactions: an overview
Bariwal, Jitender
Van der Eycken, Erik
[J]. CHEMICAL SOCIETY REVIEWS, 2013, 42 (24) : 9283 - 9303
[4] Selected Copper-Based Reactions for C-N, C-O, C-S, and C-C Bond Formation
Bhunia, Subhajit
Pawar, Govind Goroba
Kumar, S. Vijay
Jiang, Yongwen
Ma, Dawei
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (51) : 16136 - 16179
[5] Catalytic racemisation of chiral amines and application in dynamic kinetic resolution
Blacker, A. John
Stirling, Matthew J.
Page, Michael I.
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (03) : 642 - 648
[6] New N- and O-arylations with phenylboronic acids and cupric acetate
Chan, DMT
Monaco, KL
Wang, RP
Winters, MP
[J]. TETRAHEDRON LETTERS, 1998, 39 (19) : 2933 - 2936
[7] Lipase/palladium-catalyzed asymmetric transformations of ketoximes to optically active amines
Choi, YK
Kim, MJ
Ahn, Y
Kim, MJ
[J]. ORGANIC LETTERS, 2001, 3 (25) : 4099 - 4101
[8] Breaking Amides using Nickel Catalysis
Dander, Jacob E.
Garg, Neil K.
[J]. ACS CATALYSIS, 2017, 7 (02): : 1413 - 1423
[9] Chan-Evans-Lam Couplings with Copper Iminoarylsulfonate Complexes: Scope and Mechanism
Duparc, Valerie Hardouin
Bano, Guillaume L.
Schaper, Frank
[J]. ACS CATALYSIS, 2018, 8 (08): : 7308 - 7325
[10] Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine
Evans, DA
Katz, JL
West, TR
[J]. TETRAHEDRON LETTERS, 1998, 39 (19) : 2937 - 2940

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