Formation of Carbonyl Compounds from Amines through Oxidative C-N Bond Cleavage using Visible Light Photocatalysis and Applications to N-PMB-Amide Deprotection

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57
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58

초록

A method has been developed for C-N bond cleavage that utilizes visible light photocatalysis. The process, which utilizes 1 mol% of the ruthenium complex Ru(bpy)(3)Cl-2 as the photocatalyst, potassium persulfate (K2S2O8) as the oxidant and water/acetonitrile (H2O/CH3CN) as the solvent, transforms a variety of primary, secondary and tertiary amines to the corresponding carbonyl compounds. In addition, this method was applied to the removal of a p-methoxylbenzyl (PMB) group from N-PMB protected amides.

키워드

carbonyl compounds; C-N bond cleavage; photocatalysis; PMB deprotection; visible light; PHOTOREDOX CATALYSIS; AEROBIC OXIDATION; CONTINUOUS-FLOW; TRANSAMINATION REACTION; RADICAL CONDITIONS; HYDROGEN-PEROXIDE; ELECTRON-TRANSFER; TERTIARY-AMINES; ACTIVE-SITE; H ARYLATION
제목
Formation of Carbonyl Compounds from Amines through Oxidative C-N Bond Cleavage using Visible Light Photocatalysis and Applications to N-PMB-Amide Deprotection
저자
Iqbal, Naeem; Cho, Eun Jin
DOI
10.1002/adsc.201500257
발행일
2015-07
유형
Article
저널명
Journal für Praktische Chemie
권
357
호
10
페이지
2187 ~ 2192