Journal
ACS CATALYSIS
Volume 11, Issue 17, Pages 10847-10854Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c02653
Keywords
iridium(III); quinoid carbene; N-arylation; migratory insertion; phenol/naphthol
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Funding
- SERB, India [CRG/2018/000630]
- DST, India [SR/FST/CSII-026/2013]
- IIT Kharagpur
- Ministry of Electronics and Information Technology (MeitY)
- Department of Science and Technology (DST), Government of India
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This study demonstrates an efficient Ir(III)-catalyzed straightforward intermolecular N-arylation of acyclic aliphatic amides using quinone diazide as a coupling partner. The reaction conditions are simple and mild with a broad substrate scope, and the bidentate picolinamide group is essential for successful transformation. Mechanistic studies and DFT calculations highlight a migratory insertion-based pathway. The developed method exhibits different reactivities compared to reactions using related diazo/azide congeners under Rh(III)/Ir(III) catalysis.
An efficient Ir(III)-catalyzed straightforward intermolecular N-arylation of acyclic aliphatic amides has been achieved using quinone diazide as a coupling partner. The reaction has been developed under simple and mild reaction conditions with a broad substrate scope. The bidentate picolinamide group is essential for successful transformation. Mechanistic studies and DFT calculations highlighted the migratory insertion-based pathway. The developed method exhibits different reactivities compared to the reactions of acyclic aliphatic amides using related diazo/azide congeners under Rh(III)/Ir(III) catalysis.
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