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Controlled Relay Process to Access N-Centered Radicals for Catalyst-free Amidation of Aldehydes under Visible Light

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Title
Controlled Relay Process to Access N-Centered Radicals for Catalyst-free Amidation of Aldehydes under Visible Light
Author(s)
Wongyu Lee; Hyun Ji Jeon; Hoimin Jung; Dongwook Kim; Sangwon Seo; Sukbok Chang
Subject
AMIDE BOND FORMATION, ; C-H AMINATION, ; MEDIATED SYNTHESIS, ; IMIDYL RADICALS, ; AMINES, ; ARENES, ; ACID, ; HYDROAMINATION, ; CHLOROAMIDES, ; PRECURSORS
Publication Date
2021-02-11
Journal
CHEM, v.7, no.2, pp.495 - 508
Publisher
CELL PRESS
Abstract
Nitrogen-centered radicals have attracted increasing attention as a versatile reactive intermediate for diverse C-N bond constructions. Despite the significant advances achieved in this realm, the controllable formation of such species under catalyst-free conditions remains highly challenging. Here, we report a new relay process involving the slow in situ generation of a photoactive N-chloro species via C-N bond formation, which subsequently enables mild and selective access to N-centered radicals under visible light conditions. The utility of this approach is demonstrated by the conversion of aldehydes to amides, employing N-chloro-N-sodio carbamates as a practical amidating source. This synthetic operation obviates the need for catalysts, external oxidants, and coupling reagents that are typically required in related processes, consequently allowing high functional group tolerance and excellent applicability for late-stage functionalization.
URI
https://pr.ibs.re.kr/handle/8788114/9199
DOI
10.1016/j.chempr.2020.12.004
ISSN
2451-9294
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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