Triethyl Phosphite/Benzoyl Peroxide Mediated Reductive Dealkylation ofO-Benzoylhydroxylamines: A Cascade Synthesis of Secondary Amides

A new triethyl phosphite/benzoyl peroxide (BPO) mediated system has been developed for the synthesis of secondary amides with good to excellent yields in a single step. This unprecedented cascade process involves sequential reduction of N-O bond and benzoylation followed by dealkylation of N-C bond...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2020; no. 27; pp. 4235 - 4238
Main Authors Aegurla, Balakrishna, Mandle, Ram D., Shinde, Prasad G., Parit, Ratan S., Kamble, Sanjay P., Sudalai, Arumugam, Senthilkumar, Beeran
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 23.07.2020
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PRACTICAL SYNTHESIS
Redox reactions
AMINES
DEBENZYLATION
AMIDATION
Amides
O-Benzoylhydroxylamines
Synthetic methods
DEPROTECTION
Cascade reactions
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Summary:A new triethyl phosphite/benzoyl peroxide (BPO) mediated system has been developed for the synthesis of secondary amides with good to excellent yields in a single step. This unprecedented cascade process involves sequential reduction of N-O bond and benzoylation followed by dealkylation of N-C bond ofO-benzoylhydroxylamines (O-BHA). The methodology is versatile as it tolerates a variety of aromatic and aliphaticO-BHA as substrates to access secondary amides.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202000611