Dual Intermolecular Allylic C–H Functionalization of the Tetrasubstituted Alkene Scaffold | Zendy

Martínez Claudio | Zendy; Muñiz Kilian | Zendy

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Dual Intermolecular Allylic C–H Functionalization of the Tetrasubstituted Alkene Scaffold

Author(s) -

Martínez Claudio,

Muñiz Kilian

Publication year - 2018

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201701624

Subject(s) - chemistry , allylic rearrangement , chemoselectivity , surface modification , alkene , reagent , intermolecular force , combinatorial chemistry , organic chemistry , catalysis , molecule

Activation of chloramine‐T (TsNNaCl) with a Brønsted acid generates an active reagent for the double allylic C–H functionalization of tetrasubstituted alkenes in an intermolecular manner. The reaction generates a carbon–nitrogen and a carbon–chlorine bond, and proceeds with complete regio‐ and chemoselectivity. A total of 14 examples demonstrate the applicability of the dual C–H functionalization process. The mechanism involves the intermediacy of a 1,3‐butadiene derivative; 1,3‐butadienes can also be used directly as substrates.

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