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Synthesis 2024; 56(11): 1711-1718
DOI: 10.1055/s-0042-1751512
paper
New Trends in Organic Synthesis from Chinese Chemists

Visible-Light-Enabled Radical Alkynylborylation of Activated Alkenes

Congjun Zhu
a   School of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou, Henan 450001, P. R. of China
b   State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering,Nanjing University, Nanjing 210023, P. R. of China
,
Shunruo Yao
b   State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering,Nanjing University, Nanjing 210023, P. R. of China
,
Jin Xie∗
b   State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering,Nanjing University, Nanjing 210023, P. R. of China
› Author AffiliationsFunding: National Key Research and Development Program of China (2021YFC2101901); National Natural Science Foundation of China (22202060, 22122103, 21971108); Fundamental Research Funds for the Central Universities (020514380304, 020514380232, 020514380272); Funding Plan of Key Scientific Research Project of Colleges and Universities in Henan Province (23A150029); Doctoral Scientific Research Start-up Foundation from Henan University of Technology (2021BS080).
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Abstract

A photoredox-catalyzed protocol for performing radical difunctionalization of alkenes using N-heterocyclic carbene (NHC) boranes and alkynyl bromines is described. The alkynylborylation difunctionalization reaction involves photoredox generation of boryl radical, with subsequent radical addition to the double bond followed by the capture of alkynyl bromide to form a C–C bond. This method features mild reaction conditions, remarkable chemoselectivity, broad substrate scope and good to excellent yields (up to 89%). The modification of coumarin derivatives indicates that this approach can provide a useful route for the synthesis of complex alkynylborylated products.

Key words

photoredox catalysis - N-heterocyclic carbene boranes - alkynyl bromides - radical reaction - difunctionalization

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751512.
  • Supporting Information


Publication History

Received: 11 August 2023

Accepted after revision: 20 September 2023

Article published online:
31 October 2023

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