Using IR vibrations to quantitatively describe and predict site-selectivity in multivariate Rh-catalyzed C-H functionalization

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Abstract

Achieving selective C-H functionalization is a significant challenge that requires discrimination between many similar C-H bonds. Yet, reaction systems employing Rh<inf>2</inf>(DOSP)<inf>4</inf> and Rh<inf>2</inf>(BPCP)<inf>4</inf> were recently demonstrated to afford high levels of selectivity in the C-H insertion of carbenes into toluene-derived substrates. Herein, we explore the origin of this selectivity through a systematic analysis of substrate and reagent features that alter levels of selectivity from 20:1 to 1:610 for secondary (or tertiary)-to-primary benzylic C-H functionalization of toluene derivatives. Describing this variation using infrared vibrations and point charges, we have developed a mathematical model from which are identified features of the systems that determine levels of site-selectivity and are applied as predictive factors to describe the selectivity behavior of new substrate/reagent combinations.

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Bess, E. N., Guptill, D. M., Davies, H. M. L., & Sigman, M. S. (2015). Using IR vibrations to quantitatively describe and predict site-selectivity in multivariate Rh-catalyzed C-H functionalization. Chemical Science, 6(5), 3057–3062. https://doi.org/10.1039/c5sc00357a

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