Selective -Oxyamination and Hydroxylation of Aliphatic Amides

Compared to the -functionalization of aldehydes, ketones, even esters, the direct -modification of amides is still a challenge because of the low acidity of -CH groups. The -functionalization of N-H (primary and secondary) amides, containing both an unactived -C-H bond and a competitively active N-H...

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Published inAngewandte Chemie International Edition Vol. 56; no. 40; pp. 12307 - 12311
Main Authors Li, Xinwei, Lin, Fengguirong, Huang, Kaimeng, Wei, Jialiang, Li, Xinyao, Wang, Xiaoyang, Geng, Xiaoyu, Jiao, Ning
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 25.09.2017
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Acidity
Aldehydes
Aliphatic compounds
Amides
Chemical bonds
Chemistry
Chemistry, Multidisciplinary
Esters
Hydrogen bonds
Hydroxylation
Ketones
Physical Sciences
Preservation
Science & Technology
ELECTROPHILIC ACTIVATION
amides
EPSILON-CAPROLACTAM
radicals
BOND-FORMING REACTIONS
CHEMOSELECTIVE SYNTHESIS
TRIFLIC ANHYDRIDE
C-H functionalization
ARYLBORONIC ACIDS
oxidations
SECONDARY AMIDES
OXOAMMONIUM SALTS
ASYMMETRIC ALKYLATION
EQUILIBRIUM ACIDITIES
synthetic methods
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Summary:Compared to the -functionalization of aldehydes, ketones, even esters, the direct -modification of amides is still a challenge because of the low acidity of -CH groups. The -functionalization of N-H (primary and secondary) amides, containing both an unactived -C-H bond and a competitively active N-H bond, remains elusive. Shown herein is the general and efficient oxidative -oxyamination and hydroxylation of aliphatic amides including secondary N-H amides. This transition-metal-free chemistry with high chemoselectivity provides an efficient approach to -hydroxy amides. This oxidative protocol significantly enables the selective functionalization of inert -C-H bonds with the complete preservation of active N-H bond.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 14
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201706963