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Synlett 2024; 35(16): 1839-1843
DOI: 10.1055/a-2236-5948
DOI: 10.1055/a-2236-5948
synpacts
Precision Alkynylation of 1,3-Bis(Boronates) by Utilizing Distinct Organometallic Reagents for Regioselective Synthesis
We are grateful for financial support from NSFC (Grant No. 22101177), the Science and Technology Commission of Shanghai Municipality (Grants Nos. 21ZR1442000 and 23YF1426700), and startup funding from ShanghaiTech University.
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 - photocatalysisPublication History
Received: 11 December 2023
Accepted after revision: 29 December 2023
Accepted Manuscript online:
29 December 2023
Article published online:
26 January 2024
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