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Highly Selective and Catalytic C-N Bond Cleavage of Tertiary Sulfonamides: Scope and Mechanistic Insight.

ABSTRACT: A highly chemoselective C-N bond cleavage reaction of p-methoxybenzyl- (PMB), 3,4-dimethoxybenzyl- (DMB), or cinnamyl-substituted tertiary sulfonamides in the presence of catalytic Bi(OTf)₃ is presented. A wide range of sulfonamide substrates smoothly furnished the corresponding C-N bond cleavage products in good to excellent yields. Great efforts have been made to obtain insights into the reaction mechanism based on a series of control experiments and mass spectroscopy.

SUBMITTER: Bhattacharya A

PROVIDER: S-EPMC8320137 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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Highly Selective and Catalytic C-N Bond Cleavage of Tertiary Sulfonamides: Scope and Mechanistic Insight.

Bhattacharya Aditya A Shukla Pushpendra Mani PM Maji Biswajit B

ACS omega 20210716 29

A highly chemoselective C-N bond cleavage reaction of <i>p</i>-methoxybenzyl- (PMB), 3,4-dimethoxybenzyl- (DMB), or cinnamyl-substituted tertiary sulfonamides in the presence of catalytic Bi(OTf)<sub>3</sub> is presented. A wide range of sulfonamide substrates smoothly furnished the corresponding C-N bond cleavage products in good to excellent yields. Great efforts have been made to obtain insights into the reaction mechanism based on a series of control experiments and mass spectroscopy. ...[more]

PMID: 34337238

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