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Published on: January 19, 2016
Shuttle Hydrogen Atom Transfer for Hydro-Fluorosulfonylation of Haloalkynes without β-Scission
Tianyu He1, Yi Duan1, Qixin Jia1
1State Key Laboratory for Development and Utilization of Forest Food Resources, Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037, China.
Abstract:
Radical addition to haloalkynes often produces alkynylation products with the cleavage of these halogen groups. Herein, we report a direct hydrogen atom transfer (d-HAT) photocatalysis-enabled shuttle HAT system that realizes hydro-fluorosulfonylation of alkynyl bromides and chlorides without β-scission. Our regio- and stereoselective hydro-fluorosulfonylation strategy enables facile access to α-halo sulfonyl fluorides, which are challenging to synthesize with previous methods. The retention of these bromo and chloro substituents enables versatile downstream transformations.
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