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Visible-Light-Mediated Radical trans-Hydroboration of Alkynes with NHC Borane
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-12-19 , DOI: 10.1021/acs.joc.4c02577 Xin Wu, Zhang Chen, Xue Peng, Zhen Wang, Yao-Fu Zeng
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-12-19 , DOI: 10.1021/acs.joc.4c02577 Xin Wu, Zhang Chen, Xue Peng, Zhen Wang, Yao-Fu Zeng
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Although the radical hydroboration of alkenes with N-heterocyclic carbene (NHC) borane is well documented, the radical hydroboration of alkynes, especially terminal alkynes, remains challenging. Herein, a photoredox-catalyzed radical trans-hydroboration of alkynes with NHC borane has been developed, which provided various alkenyl boron compounds in moderate to good yields. This protocol exhibits a broad substrate scope, as both internal and terminal alkynes were compatible. The synthetic value of this method was further demonstrated by its applicability in the late-stage modification of bioactive molecules. A preliminary mechanism for this reaction was proposed.
更新日期：2024-12-20
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