Premium
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.