Nickel‐Catalyzed Directed Benzylation of Ortho C−H Bonds in Aromatic Amides through C−H/C−N Cleavage. Issue 1 (29th November 2017)

• Record Type: Journal Article
• Authors: Li, Jiawei; Zheng, Zhaojing; Xiao, Tiantian; Xu, Peng‐Fei; Wei, Hao
• Is Part Of: Asian journal of organic chemistry. Volume 7:Issue 1(2018)
• Page Start: 133
• Page End: 136
• Publication Date: 2017-11-29
• Subjects: ammonium salts -- benzylation -- C−N bond cleavage -- cross-coupling -- nickel catalysis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201700569
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: The cleavage of both sp 2 C−H and C−N bonds by a nickel‐catalyzed reaction of aromatic amides containing an 8‐aminoquinoline moiety with benzyl ammonium salts is reported. A wide variety of functional groups are tolerated in the reaction. Preliminary mechanistic investigations indicate that the reaction probably proceeds through a Ni I /Ni III catalytic pathway. This Ni‐catalyzed procedure provides an alternative approach to construct diarylmethane derivatives. Abstract : Double action : Cross‐coupling of aromatic amides with aryltrimethylammonium salts through the cleavage of both sp 2 C−H and C−N bonds is achieved in the presence of 10 mol % of NiBr2 as a simple, inexpensive, and abundant catalyst.