首页|Photocatalytic C(sp3)-H gem-Difluoroallylation and Alkylation with Alkenes via a Base-Assisted Formal 1,2-Hydrogen Atom Transfer of Amidyl Radicals
Photocatalytic C(sp3)-H gem-Difluoroallylation and Alkylation with Alkenes via a Base-Assisted Formal 1,2-Hydrogen Atom Transfer of Amidyl Radicals
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Compared to well-established 1,5-HAT of N-centered radicals,the synthetic applications of 1,2-HAT process were scarce due to the high barrier and constrained three-membered transition state.Here,we have developed a novel C(sp3)-H gem-difluoroallylation via a base assisted formal 1,2-HAT of amidyl radicals with the reductive quenching cycle of photocatalyst.This transformation enables the efficient formation of a-aminoalkyl radicals via 1,2-HAT and showcases good functional group tolerance.Our preliminary mechanistic experiments,along with Density Functional Theory(DFT)calculations demonstrate the feasibility of 1,2-HAT of amidyl radicals,espe-cially when assisted by a base.Furthermore,our method also succeeds in the Giese addition of electron-deficient alkenes as well as styrene.
12-Hydrogen atom transferAmidyl radicalsgem-DifluoroallylationAlkenesPhotocatalysisDefluoroalkylation
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials,College of Chemistry and Materials Sciences,Zhejiang Normal University,688 Ying bin Road,Jinhua,Zhejiang 321004,China
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