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Synthesis 2024; 56(11): 1711-1718
DOI: 10.1055/s-0042-1751512
DOI: 10.1055/s-0042-1751512
paper
New Trends in Organic Synthesis from Chinese Chemists
Visible-Light-Enabled Radical Alkynylborylation of Activated Alkenes
Funding: 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).
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 - difunctionalizationSupporting 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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Thermal conditions, selected examples:
Photoredox conditions, selected examples: