Rh-Catalyzed Regioselective Dialkylation of Cage B–H bonds in o‑Carboranes: Oxidative Heck Reactions via an Enol Isomerization

In the presence of a carboxylic acid directing group, Rh-catalyzed regioselective directed dialkylation of B­(4,5)–H bonds in o-carboranes and oxidative coupling with allylic alcohols is reported. This strategy constructs a series of 4,5-dialkylated o-carboranes in good yields with excellent regiose...

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Published inOrganic letters Vol. 21; no. 19; pp. 8018 - 8021
Main Authors Wang, Qian, Tian, Song, Zhang, Chuyi, Li, Jiangwei, Wang, Zhixuan, Du, Yongmei, Zhou, Ling, Lu, Jian
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 04.10.2019
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Summary:In the presence of a carboxylic acid directing group, Rh-catalyzed regioselective directed dialkylation of B­(4,5)–H bonds in o-carboranes and oxidative coupling with allylic alcohols is reported. This strategy constructs a series of 4,5-dialkylated o-carboranes in good yields with excellent regioselectivity. A possible catalytic cycle is proposed that involves a tandem sequence of Rh-catalyzed cage B–H activation, alkene insertion, selective β-H elimination, enol isomerization, and decarboxylation.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03009