Balancing Reactivity, Regioselectivity, and Product Stability in Ir-Catalyzed Ortho-C–H Borylations of Anilines by Modulating the Diboron Partner

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...

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Published inOrganic letters Vol. 26; no. 26; pp. 5420 - 5424
Main Authors Montero Bastidas, Jose R., Yadav, Anshu, Lee, Seokjoo, Ghaffari, Behnaz, Smith, Milton R., Maleczka, Robert E.
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 05.07.2024
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Letter
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Summary: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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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c01495