Center for Selective C–H Functionalization
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Non-Directed Allylic C-H Acetoxylation in the Presence of Lewis Basic Heterocycles.

Malik, Hasnain A Taylor, Buck L H Kerrigan, John R Grob, Jonathan E Houk, K N Du Bois, J Hamann, Lawrence G Patterson, Andrew W

Published in Chemical science

We outline a strategy to enable non-directed Pd(II)-catalyzed C-H functionalization in the presence of Lewis basic heterocycles. In a high-throughput screen of two Pd-catalyzed C-H acetoxylation reactions, addition of a variety of N-containing heterocycles is found to cause low product conversion. A pyridine-containing test substrate is selected as...

Using IR vibrations to quantitatively describe and predict site-selectivity in multivariate Rh-catalyzed C-H functionali... PDF available through Get Fulltext Research

Bess, Elizabeth N Guptill, David M Davies, Huw M L Sigman, Matthew S

Published in Chemical science

Achieving selective C-H functionalization is a significant challenge that requires discrimination between many similar C-H bonds. Yet, reaction systems employing Rh2(DOSP)4 and Rh2(BPCP)4 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...

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