Copper-Catalyzed Oxidative Coupling of Formamides with Salicylaldehydes: Synthesis of Carbamates in the Presence of a Sensitive Aldehyde Group

A diverse library of novel carbamates was synthesized utilizing copper-catalyzed oxidative C–O coupling of formamides and salicylaldehydes. Sensitive aldehyde groups remained intact in the presence of an oxidant and a transition-metal salt. Salicylaldehydes bearing electron-donating, electron-withdr...

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Published inJournal of organic chemistry Vol. 79; no. 7; pp. 3206 - 3214
Main Authors Barve, Balaji D, Wu, Yang-Chang, El-Shazly, Mohamed, Chuang, Da-Wei, Cheng, Yuan-Bin, Wang, Jeh-Jeng, Chang, Fang-Rong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.04.2014
Amer Chemical Soc
Subjects
Aldehydes - chemistry
Carbamates - chemical synthesis
Carbamates - chemistry
Catalysis
Chemistry
Chemistry, Organic
Copper - chemistry
Formamides - chemistry
Molecular Structure
Oxidative Coupling
Physical Sciences
Science & Technology
H BOND ACTIVATION
REARRANGEMENT
ALCOHOLS
N,N-DIMETHYLFORMAMIDE
AMINES
EFFICIENT
ACCESS
C-H
CARBOXYLIC-ACIDS
WATER
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Summary:A diverse library of novel carbamates was synthesized utilizing copper-catalyzed oxidative C–O coupling of formamides and salicylaldehydes. Sensitive aldehyde groups remained intact in the presence of an oxidant and a transition-metal salt. Salicylaldehydes bearing electron-donating, electron-withdrawing, and halogen groups as well as 1-hydroxy-2-naphthaldehydes provided the desired carbamates in good to excellent yields.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo402798k