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Published on: November 9, 2019
Balancing Reactivity, Regioselectivity, and Product Stability in Ir-Catalyzed Ortho-C-H Borylations of Anilines by
Jose R Montero Bastidas1, Anshu Yadav1, Seokjoo Lee1
1Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824, United States.
Abstract:
Ir-catalyzed arene C-H borylations (CHB) of anilines can be highly ortho selective by using a small B2eg2 (eg = ethane-1,2-diol) as the borylating reagent. Unfortunately, the products are prone to decomposition, and transesterification with pinacol is required prior to isolation. This work offers a solution by adjusting the size of the diboron reagent. Based on our evaluation, we conclude that B2bg2 (bg = butane-1,2-diol) achieves an optimal balance between CHB regioselectivity and stability for the borylated products.
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