One of the major challenges in the field of C-H Functionalization is to achieve site selectivity by catalyst control, which can overwhelm the intrinsic reactivity tendencies of the substrate. This presentation will describe the development of three types of dirhodium catalysts for the site-selective functionalization of either primary, secondary or tertiary C-H bonds. The key intermediates are rhodium-stabilized donor/acceptor carbenes, which electronically prefer reactions at tertiary sites but behave as sterically crowded systems. By increasing the steric environment around the catalyst, steric factors can be made to dominate over electronic preferences, enabling secondary or primary sites to be selectively functionalized. The full scope of these catalyst-controlled transformations will be described.

Catalyst-controlled site-selective and enantioselective C-H functionalization

255th National Meeting (2018)

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