Visible-Light-Enabled Radical Alkynylborylation of Activated Alkenes

Congjun Zhu; Shunruo Yao; Jin Xie

doi:10.1055/s-0042-1751512

Synthesis, Inhaltsverzeichnis

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

^aSchool of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou, Henan 450001, P. R. of China

^bState 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

^bState 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∗

^bState 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

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Abstract

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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

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Referenzen

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