首页|Reversing Conventional Site-Selectivity:Electrochemically Driven C(sp2)-H/C(sp3)-H Coupling with H2 Evolution
Reversing Conventional Site-Selectivity:Electrochemically Driven C(sp2)-H/C(sp3)-H Coupling with H2 Evolution
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Sustainable and site-selective C-H functionalization is still a challenge because of the comparable prop-erties of bonds of the same type.Here,an electro-chemical C(sp2)-H/C(sp3)-H coupling with aryl iodides is reported for the first time.The C(sp2)-H bond outperformed the much weaker C(sp2)-I bond participating in C(sp2)-H/C(sp3)-H coupling.This protocol features mild reaction conditions,good functional group tolerance,and scalability.Cross-coupling products with C-I bonds are versatile moi-eties for further synthetic manipulation,that can undergo Suzuki,Sonogashira,Ullmann-Ma,Catellani,Heck reactions,and so on to introduce new function-al groups into target molecules with good yields.Mechanistic investigations showed that the site selectivity of the reaction is enabled by an iodine-assisted[3,3]-sigmatropic rearrangement,and the interaction of hypervalent iodine generated in situ with an enolate is the rate-determining step.
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