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Expeditious and Solvent‐Free Nickel‐Catalyzed C−H Arylation of Arenes and Indoles
Author(s) -
Jagtap Rahul A.,
Soni Vineeta,
Punji Benudhar
Publication year - 2017
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201700321
Subject(s) - chemistry , catalysis , nickel , indole test , combinatorial chemistry , solvent , carbazole , halide , organic chemistry
Abstract An efficient solvent‐free nickel‐catalyzed method for C−H bond arylation of arenes and indoles has been developed, which proceeds expeditiously through chelation assistance. The reaction is highly selective for mono‐arylation and tolerates sensitive and structurally diverse functionalities, such as halides, ethers, amines, indole, pyrrole and carbazole. This reaction represents the first example of a nickel‐catalyzed C−H arylation by monochelate assistance and symbolizes a rare precedent in solvent‐free C−H arylation. Mechanistic investigations by various controlled reactions, kinetic studies, and deuterium labeling experiments suggest that the arylation follows a single electron transfer (SET) pathway involving the turnover‐limiting C−H nickelation process.