Open AccessCarbonylative N-Heterocyclization via Nitrogen-Directed C–C Bond Activation of Nonactivated Cyclopropanes
Author(s) -
Adam D. J. Calow,
David Dailler,
John F. Bower
Publication year - 2022
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.2c02921
Subject(s) - chemistry , nitrogen , medicinal chemistry , organic chemistry
Under Rh-catalyzed conditions, secondary amines and anilines function as directing groups to facilitate regioselective C-C bond activation of nonactivated cyclopropanes. The resulting amino-stabilized rhodacycles undergo carbonylative C-N bond formation en route to challenging seven- and eight-membered lactams. The processes represent rare examples where C-C bond oxidative addition of nonactivated cyclopropanes is exploited in reaction design.