Synlett 2023; 34(09): 1023-1028
DOI: 10.1055/a-2009-8279
letter

Divergent Functionalization of Alkynes Enabled by Organic Photoredox Catalysis

,
Siran Qian
,
Financial support was provided in part by the National Institutes of Health (NIGMS) Award R35 GM136330.


Abstract

Direct functionalization of alkynes under oxidative conditions is challenging, as alkynes are usually recalcitrant towards typical oxidants. Herein, we communicate a strategy for the divergent functionalization of alkynes with photoexcited acridinium organic dyes, presumably via the formation of vinyl cation radicals as key intermediates. Based on the nature of the nucleophiles, different types of difunctionalized products were obtained in moderate to good yields. Addition of lithium Lewis acids resulted in a surprising reversal of diastereocontrol.

Supporting Information



Publication History

Received: 07 December 2022

Accepted after revision: 09 January 2023

Accepted Manuscript online:
09 January 2023

Article published online:
31 January 2023

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