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Visible-light-mediated remote aliphatic C−H functionalizations through a 1,5-hydrogen transfer cascade


Shu, Wei; Nevado, Cristina (2017). Visible-light-mediated remote aliphatic C−H functionalizations through a 1,5-hydrogen transfer cascade. Angewandte Chemie Internationale Edition, 56(7):1881-1884.

Abstract

A redox-neutral, light-mediated functionalization of unactivated C(sp3 )-H bonds via iminyl radicals is presented here. A 1,5-H transfer followed by the functionalization of a C(sp2 )-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(sp3 )-N bond formation upon a careful choice of the reaction additives.

Abstract

A redox-neutral, light-mediated functionalization of unactivated C(sp3 )-H bonds via iminyl radicals is presented here. A 1,5-H transfer followed by the functionalization of a C(sp2 )-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(sp3 )-N bond formation upon a careful choice of the reaction additives.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:General Chemistry, Catalysis
Language:English
Date:2017
Deposited On:04 Jan 2018 19:35
Last Modified:19 Aug 2018 12:22
Publisher:Wiley-VCH Verlag
ISSN:1433-7851
OA Status:Closed
Publisher DOI:https://doi.org/10.1002/anie.201609885
PubMed ID:28097790

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