In our efforts to address the poor monoselective generally observed in C-H iodinations of benzoic acids, we have developed a highly monoselective iridium-catalyzed C-H iodination methodology. The utility of the method was showcased with a broad scope of <i>para- </i>and <i>meta-</i>substituted benzoic acids, which were transformed with &gt;20:1 mono:di selectivity. Moreover, functionalization proximal to the carboxylate directing group was shown to be favored even in the presence of potential competing directing groups. A mechanistic study was carried out, providing insights into the reaction mechanism, including the elucidation of the resting state, turnover-limiting step, and the cause of monoselectivity.

Iridium-catalyzed monoselective C-H iodination of benzoic acids: Development and mechanistic investigation

2019 Fall National Meeting

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