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Nickel-Catalyzed Alkynylation of a C(sp2)–H Bond Directed by an 8-Aminoquinoline Moiety

Author:
Yi, Jun, Yang, Li, Xia, Chungu, Li, Fuwei
Source:
Journal of organic chemistry 2015 v.80 no.12 pp. 6213-6221
ISSN:
1520-6904
Subject:
aldehydes, alkynes, amides, aminoquinolines, catalysts, ligands, moieties, nickel, organic chemistry
Abstract:
An efficient nickel catalyst system for the direct ortho C–H alkynylation of the amides has been successfully developed with the directing assistance of 8-aminoquinoline. It was found that the flexible bis(2-dimethylaminoethyl) ether (BDMAE) ligand was critical to achieve the optimized reactivity. This protocol showed good tolerance toward not only a wide range of (hetero)aryl amides but also the rarely studied α,β-unsaturated alkenyl amide. The directing amide group could be easily transformed to aldehyde or ester in high yields. Meanwhile, the removable TIPS substituent on the resultant aryl/alkenyl alkynes could be further converted to an aryl moiety through a Sila–Sonogashira coupling reaction. This Ni-catalyzed alkynylation procedure provides an alternative approach to construct a C(sp²)–C(sp) bond.
Agid:
5503721