Nitrate promoted mild and versatile Pd-catalysed C(sp)-H oxidation with carboxylic acids

A nitrate-promoted Pd-catalysed mild cross-dehydrogenative C(sp 2 )-H bond oxidation of oximes or azobenzenes with diverse carboxylic acids has been developed. In contrast to the previous catalytic systems, this protocol features mild conditions (close to room temperature for most cases) and a broad...

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Published inOrganic & biomolecular chemistry Vol. 18; no. 34; pp. 6732 - 6737
Main Authors Xiong, Xue, Mao, Yang-Jie, Hao, Hong-Yan, He, Yu-Ting, Xu, Zhen-Yuan, Luo, Gen, Lou, Shao-Jie, Xu, Dan-Qian
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 14.09.2020
Royal Society of Chemistry
Subjects
Aromatic compounds
Carboxylic acids
Chemistry
Chemistry, Organic
Computer applications
Dehydrogenation
Esters
Hydrogen bonds
Nitrates
Oxidation
Oximes
Physical Sciences
Room temperature
Science & Technology
Substrates
ACTIVATION
DIRECT ACYLOXYLATION
NOX
BONDS
ARYL
C-H
BENZOXYLATION
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Summary:A nitrate-promoted Pd-catalysed mild cross-dehydrogenative C(sp 2 )-H bond oxidation of oximes or azobenzenes with diverse carboxylic acids has been developed. In contrast to the previous catalytic systems, this protocol features mild conditions (close to room temperature for most cases) and a broad substrate scope (up to 64 examples), thus constituting a versatile method to directly prepare diverse O -aryl esters. Moreover, the superiority of the nitrate additive in this mild transformation was further determined by experimental and computational evidence. A nitrate-promoted Pd-catalysed cross-dehydrogenative C(sp 2 )-H oxidation of oximes or azobenzenes with diverse aromatic and aliphatic acids was developed, allowing the versatile formation of O -aryl esters under mild reaction conditions.
Bibliography:10.1039/d0ob01124j
Electronic supplementary information (ESI) available. See DOI
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob01124j