Precision Alkynylation of 1,3-Bis(Boronates) by Utilizing Distinct Organometallic Reagents for Regioselective Synthesis

Ang Chen; Chong-Lei Ji; De-Wei Gao

doi:10.1055/a-2236-5948

Synlett, Table of Contents

Synlett 2024; 35(16): 1839-1843
DOI: 10.1055/a-2236-5948

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Precision Alkynylation of 1,3-Bis(Boronates) by Utilizing Distinct Organometallic Reagents for Regioselective Synthesis

Ang Chen‡

,

Chong-Lei Ji‡

,

De-Wei Gao ∗

Abstract

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Abstract

The selective functionalization of 1,3-bis(boronic) esters holds the potential for creating diverse molecular structures, particularly through the late-stage functionalization of the remaining C–B bond. By employing distinct organometallic reagents, we have developed a method for regiodivergent alkynylation of 1,3-bis(boronic) esters, facilitated by unique chelation patterns. Notably, this methodology effectively overcomes limitations commonly encountered in radical chemistry, which generates only monoselective downstream targets. Furthermore, the compounds synthesized through this approach can serve as significant building blocks, contributing to the construction of molecular complexity.

Key words

regiodivergent synthesis - alkynylation - bisboronates - organometallic reagents - C–B bond - photocatalysis

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References

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