A number of organoboronic acids are prone to decomposition under the most commonly used Suzuki-Miyaura reaction (SMC) conditions. Protected boronate substrates have been developed to address this issue, such as organotrifluoroborates and N-methyliminodiacetic acid (MIDA) boronates.Lithium triisopropyl borates (LTB) are often accessed as intermediates in the synthesis of most commonly used masked boronates. General conditions for the SMC coupling of LTB are presented as well as a procedure for a one-pot lithiation, borylation, and subsequent SMC reaction are presented.

Lithium triisopropyl borates as nucleophiles for Suzuki-Miyaura cross coupling reactions

245th National Meeting (2013)

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