Direct C-H bond functionalization is a highly desirable transformation, and recently deprotonative zincation with zinc-amide bases has been shown as a facile method to achieve many valuable transformations. Traditionally, these zinc amide bases have been synthesized from zinc chloride, which generates air and moisture-sensitive reagents. However, organozinc pivalate reagents have been found to have improved air and moisture stability and can be generated through deprotonative zincation. This works focuses on the development of a novel dicyclohexylamine zinc pivalate base (Cy2NZnOPiv) for the deprotonative zincation of sp2 and sp3 C-H bonds to generate organozinc pivalate reagents. This base is easily synthesized from inexpensive reagents and has been studied for the deprotonative zincation of heteroarenes and carbonyl derivatives. Due to the significance of phosphonates in agrochemicals and pharmaceuticals, the α functionalization of phosphonates has been explored. Organozinc pivalate intermediates have been studied for copper-catalyzed cross-coupling with hypervalent iodine reagents. This work aims to establish a facile and generalized strategy for valuable direct C-H functionalization utilizing inexpensive and readily available reagents.

Deprotonative zincation for the generation and functionalization of organozinc pivalate reagents

2019 Spring National Meeting

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.