Cu(II)-Catalyzed, Site Selective Sulfoximination to Indole and Indolines via Dual C–H/N–H Activation

Mohit Kumar; Anushka Rastogi; null Raziullah; Ashfaq Ahmad; Manoj Kumar Gangwar; Dipankar Koley

doi:10.1021/acs.orglett.2c02817

Cu(II)-Catalyzed, Site Selective Sulfoximination to Indole and Indolines via Dual C–H/N–H Activation

Mohit Kumar, Anushka Rastogi, Raziullah, Ashfaq Ahmad, Manoj Kumar Gangwar, Dipankar Koley

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

5 Scopus citations

Abstract

A copper-catalyzed protocol furnishing N-arylated sulfoximines has been developed via dual N-H/C-H activation. Arylalkyl- and less reactive diarylsulfoximines were efficiently coupled with privileged scaffolds like indolines, indoles, and N-Ar-7-azaindoles. Sulfoximines based on medicinally relevant scaffolds (phenothiazine, dibenzothiophene, thioxanthenone) were also well tolerated. Detailed mechanistic studies indicate that the deprotometalation and protodemetalation step is the reversible step.

Original language	English (US)
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.2c02817
State	Published - Nov 29 2022

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Physical and Theoretical Chemistry

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10.1021/acs.orglett.2c02817

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@article{63b1337aabd04e87ba772a7cb6c54990,

title = "Cu(II)-Catalyzed, Site Selective Sulfoximination to Indole and Indolines via Dual C–H/N–H Activation",

abstract = "A copper-catalyzed protocol furnishing N-arylated sulfoximines has been developed via dual N-H/C-H activation. Arylalkyl- and less reactive diarylsulfoximines were efficiently coupled with privileged scaffolds like indolines, indoles, and N-Ar-7-azaindoles. Sulfoximines based on medicinally relevant scaffolds (phenothiazine, dibenzothiophene, thioxanthenone) were also well tolerated. Detailed mechanistic studies indicate that the deprotometalation and protodemetalation step is the reversible step.",

author = "Mohit Kumar and Anushka Rastogi and Raziullah and Ashfaq Ahmad and Gangwar, {Manoj Kumar} and Dipankar Koley",

note = "KAUST Repository Item: Exported on 2022-12-01 Acknowledgements: Financial support from CSIR (NISTHA, MPL-2034), UGC-New Delhi (R. and M.K.), and CSIR-New Delhi (A.A. and A.R.) is gratefully acknowledged. We thank the CDRI SAIF division for analytical support. We thank Dr. Benudhar Punji, CSIR-NCL, for his helpful suggestion. CDRI Communication no 10500.",

year = "2022",

month = nov,

day = "29",

doi = "10.1021/acs.orglett.2c02817",

language = "English (US)",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

}

TY - JOUR

T1 - Cu(II)-Catalyzed, Site Selective Sulfoximination to Indole and Indolines via Dual C–H/N–H Activation

AU - Kumar, Mohit

AU - Rastogi, Anushka

AU - Raziullah, null

AU - Ahmad, Ashfaq

AU - Gangwar, Manoj Kumar

AU - Koley, Dipankar

N1 - KAUST Repository Item: Exported on 2022-12-01 Acknowledgements: Financial support from CSIR (NISTHA, MPL-2034), UGC-New Delhi (R. and M.K.), and CSIR-New Delhi (A.A. and A.R.) is gratefully acknowledged. We thank the CDRI SAIF division for analytical support. We thank Dr. Benudhar Punji, CSIR-NCL, for his helpful suggestion. CDRI Communication no 10500.

PY - 2022/11/29

Y1 - 2022/11/29

N2 - A copper-catalyzed protocol furnishing N-arylated sulfoximines has been developed via dual N-H/C-H activation. Arylalkyl- and less reactive diarylsulfoximines were efficiently coupled with privileged scaffolds like indolines, indoles, and N-Ar-7-azaindoles. Sulfoximines based on medicinally relevant scaffolds (phenothiazine, dibenzothiophene, thioxanthenone) were also well tolerated. Detailed mechanistic studies indicate that the deprotometalation and protodemetalation step is the reversible step.

AB - A copper-catalyzed protocol furnishing N-arylated sulfoximines has been developed via dual N-H/C-H activation. Arylalkyl- and less reactive diarylsulfoximines were efficiently coupled with privileged scaffolds like indolines, indoles, and N-Ar-7-azaindoles. Sulfoximines based on medicinally relevant scaffolds (phenothiazine, dibenzothiophene, thioxanthenone) were also well tolerated. Detailed mechanistic studies indicate that the deprotometalation and protodemetalation step is the reversible step.

UR - http://hdl.handle.net/10754/686046

UR - https://pubs.acs.org/doi/10.1021/acs.orglett.2c02817

U2 - 10.1021/acs.orglett.2c02817

DO - 10.1021/acs.orglett.2c02817

M3 - Article

C2 - 36444657

SN - 1523-7060

JO - Organic Letters

JF - Organic Letters

ER -

Cu(II)-Catalyzed, Site Selective Sulfoximination to Indole and Indolines via Dual C–H/N–H Activation

Abstract

ASJC Scopus subject areas

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