Synthesis of Sulfoxonium Ylides from Amides by Selective N-C(O) Activation

Md Mahbubur Rahman; Michal Szostak

doi:10.1021/acs.orglett.1c01535

Synthesis of Sulfoxonium Ylides from Amides by Selective N-C(O) Activation

Md Mahbubur Rahman, Michal Szostak

Rutgers Newark, Chemistry

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

The direct synthesis of sulfoxonium ylides from amides by selective N-C(O) cleavage is presented. The reaction proceeds through the nucleophilic addition of dimethylsulfoxonium methylide to the amide bond in acyclic twisted amides under exceedingly mild room temperature conditions. A variety of amides can be employed, and the protocol can be applied to the late-stage derivatization of pharmaceuticals. Mechanistic studies outline the relative order of reactivity of amides.

Original language	English (US)
Pages (from-to)	4818-4822
Number of pages	5
Journal	Organic letters
Volume	23
Issue number	12
DOIs	https://doi.org/10.1021/acs.orglett.1c01535
State	Published - Jun 18 2021

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.1c01535

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title = "Synthesis of Sulfoxonium Ylides from Amides by Selective N-C(O) Activation",

abstract = "The direct synthesis of sulfoxonium ylides from amides by selective N-C(O) cleavage is presented. The reaction proceeds through the nucleophilic addition of dimethylsulfoxonium methylide to the amide bond in acyclic twisted amides under exceedingly mild room temperature conditions. A variety of amides can be employed, and the protocol can be applied to the late-stage derivatization of pharmaceuticals. Mechanistic studies outline the relative order of reactivity of amides. ",

author = "Rahman, {Md Mahbubur} and Michal Szostak",

note = "Funding Information: We thank the NSF (CAREER CHE-1650766) and Rutgers University for support. The Bruker 500 MHz spectrometer used in this study was supported by the NSF-MRI (CHE-1229030). Additional support was provided by the Rutgers Graduate School in the form of Dean{\textquoteright}s Dissertation Fellowship. Publisher Copyright: {\textcopyright} ",

year = "2021",

month = jun,

day = "18",

doi = "10.1021/acs.orglett.1c01535",

language = "English (US)",

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T1 - Synthesis of Sulfoxonium Ylides from Amides by Selective N-C(O) Activation

AU - Rahman, Md Mahbubur

AU - Szostak, Michal

N1 - Funding Information: We thank the NSF (CAREER CHE-1650766) and Rutgers University for support. The Bruker 500 MHz spectrometer used in this study was supported by the NSF-MRI (CHE-1229030). Additional support was provided by the Rutgers Graduate School in the form of Dean’s Dissertation Fellowship. Publisher Copyright: ©

PY - 2021/6/18

Y1 - 2021/6/18

N2 - The direct synthesis of sulfoxonium ylides from amides by selective N-C(O) cleavage is presented. The reaction proceeds through the nucleophilic addition of dimethylsulfoxonium methylide to the amide bond in acyclic twisted amides under exceedingly mild room temperature conditions. A variety of amides can be employed, and the protocol can be applied to the late-stage derivatization of pharmaceuticals. Mechanistic studies outline the relative order of reactivity of amides.

AB - The direct synthesis of sulfoxonium ylides from amides by selective N-C(O) cleavage is presented. The reaction proceeds through the nucleophilic addition of dimethylsulfoxonium methylide to the amide bond in acyclic twisted amides under exceedingly mild room temperature conditions. A variety of amides can be employed, and the protocol can be applied to the late-stage derivatization of pharmaceuticals. Mechanistic studies outline the relative order of reactivity of amides.

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JO - Organic Letters

JF - Organic Letters

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ER -

Synthesis of Sulfoxonium Ylides from Amides by Selective N-C(O) Activation

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