Visible‐Light‐Mediated Remote Aliphatic C−H Functionalizations through a 1,5‐Hydrogen Transfer Cascade | Zendy

Shu Wei | Zendy; Nevado Cristina | Zendy

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Visible‐Light‐Mediated Remote Aliphatic C−H Functionalizations through a 1,5‐Hydrogen Transfer Cascade

Author(s) -

Shu Wei,

Nevado Cristina

Publication year - 2017

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201609885

Subject(s) - surface modification , chemistry , radical , photochemistry , redox , hydrogen bond , cascade , visible spectrum , aqueous medium , combinatorial chemistry , aqueous solution , organic chemistry , molecule , materials science , optoelectronics , chromatography

A redox‐neutral, light‐mediated functionalization of unactivated C(sp 3 )−H bonds via iminyl radicals is presented here. A 1,5‐H transfer followed by the functionalization of a C(sp 2 )−H bond takes place in aqueous media producing a variety of elaborated fused ketones. Mechanistic investigations have revealed 1,5‐H transfer as the reversible, rate‐determining step in this transformation. Divergent scaffolds are also accessible via C(sp 3 )−N bond formation upon a careful choice of the reaction additives.

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