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Radical C(sp3)–H alkenylation, alkynylation and allylation of ethers and amides enabled by photocatalysis

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Abstract

An efficient radical addition/elimination reaction that enables selective incorporation of alkenyl, alkynyl and allyl functional groups into the C(sp3)–H bond under green reaction conditions is developed. The process is based on the catalytic formation of α-alkoxyl/α-amidyl radicals via the homolytic activation of the C(sp3)–H bond of ethers/amides with a catalytic amount of diarylketone in the presence of a household fluorescent light bulb. This simple reaction protocol features good functional group tolerance, scalability, convenient reagents and operating systems. Synthetic application of the method has been demonstrated via the preparation of natural products and different valuable synthones.

Graphical abstract: Radical C(sp3)–H alkenylation, alkynylation and allylation of ethers and amides enabled by photocatalysis

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Publication details

The article was received on 18 Mar 2017, accepted on 19 Apr 2017 and first published on 19 Apr 2017


Article type: Communication
DOI: 10.1039/C7GC00840F
Citation: Green Chem., 2017, Advance Article
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    Radical C(sp3)–H alkenylation, alkynylation and allylation of ethers and amides enabled by photocatalysis

    S. Paul and J. Guin, Green Chem., 2017, Advance Article , DOI: 10.1039/C7GC00840F

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