Auxiliary-Enabled Pd-Catalyzed Direct Arylation of Methylene C(sp³)–H Bond of Cyclopropanes: Highly Diastereoselective Assembling of Di- and Trisubstituted Cyclopropanecarboxamides

Abstract

An auxiliary-enabled and Pd(OAc)₂-catalyzed direct arylation of C(sp³)–H bonds of cyclopropanes and production of di- and trisubstituted cyclopropanecarboxamides having contiguous stereocenters are reported. The installation of aryl groups on cyclopropanecarboxamides led to the assembling of novel mono- and di- aryl-<i>N</i>-(quinolin-8-yl)cyclopropanecarboxamide scaffolds and mono- and di- aryl-<i>N</i>-(2-(methylthio)phenyl)cyclopropanecarboxamides. The stereochemistry of products was unequivocally assigned from the X-ray structures of key compounds