Directing Group Guided Site-Selective Diversification of Indoles by Aziridine: Synthesis of β-Indolylethylamines

Ashfaq Ahmad; Himangsu Sekhar Dutta; Mohit Kumar; null Raziullah; Manoj Kumar Gangwar; Dipankar Koley

doi:10.1021/acs.orglett.2c00120

Directing Group Guided Site-Selective Diversification of Indoles by Aziridine: Synthesis of β-Indolylethylamines

Ashfaq Ahmad, Himangsu Sekhar Dutta, Mohit Kumar, Raziullah, Manoj Kumar Gangwar, Dipankar Koley

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

8 Scopus citations

Abstract

A palladium catalyzed directing group assisted cross-coupling of aliphatic aziridines with indole, indoline, tetrahydroquinoline, and aniline has been developed to furnish the corresponding β-arylethylamine derivatives. The substrate scope was very general, and the protocol was also tolerated in the presence of various external additives. Control experiments suggested that the C-H cleavage step is the rate-determining step.

Original language	English (US)
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.2c00120
State	Published - Apr 8 2022

Bibliographical note

KAUST Repository Item: Exported on 2022-04-18
Acknowledgements: Financial support from DST-SERB (EMR/2016/000613), CSIR, and UGC-New Delhi (A.A., H.S.D., M.K., and R.) is gratefully acknowledged. We thank the CDRI SAIF division for analytical support. CDRI communication no 10389

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Physical and Theoretical Chemistry

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title = "Directing Group Guided Site-Selective Diversification of Indoles by Aziridine: Synthesis of β-Indolylethylamines",

abstract = "A palladium catalyzed directing group assisted cross-coupling of aliphatic aziridines with indole, indoline, tetrahydroquinoline, and aniline has been developed to furnish the corresponding β-arylethylamine derivatives. The substrate scope was very general, and the protocol was also tolerated in the presence of various external additives. Control experiments suggested that the C-H cleavage step is the rate-determining step.",

author = "Ashfaq Ahmad and Dutta, {Himangsu Sekhar} and Mohit Kumar and Raziullah and Gangwar, {Manoj Kumar} and Dipankar Koley",

note = "KAUST Repository Item: Exported on 2022-04-18 Acknowledgements: Financial support from DST-SERB (EMR/2016/000613), CSIR, and UGC-New Delhi (A.A., H.S.D., M.K., and R.) is gratefully acknowledged. We thank the CDRI SAIF division for analytical support. CDRI communication no 10389",

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doi = "10.1021/acs.orglett.2c00120",

language = "English (US)",

journal = "Organic Letters",

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T1 - Directing Group Guided Site-Selective Diversification of Indoles by Aziridine: Synthesis of β-Indolylethylamines

AU - Ahmad, Ashfaq

AU - Dutta, Himangsu Sekhar

AU - Kumar, Mohit

AU - Raziullah, null

AU - Gangwar, Manoj Kumar

AU - Koley, Dipankar

N1 - KAUST Repository Item: Exported on 2022-04-18 Acknowledgements: Financial support from DST-SERB (EMR/2016/000613), CSIR, and UGC-New Delhi (A.A., H.S.D., M.K., and R.) is gratefully acknowledged. We thank the CDRI SAIF division for analytical support. CDRI communication no 10389

PY - 2022/4/8

Y1 - 2022/4/8

N2 - A palladium catalyzed directing group assisted cross-coupling of aliphatic aziridines with indole, indoline, tetrahydroquinoline, and aniline has been developed to furnish the corresponding β-arylethylamine derivatives. The substrate scope was very general, and the protocol was also tolerated in the presence of various external additives. Control experiments suggested that the C-H cleavage step is the rate-determining step.

AB - A palladium catalyzed directing group assisted cross-coupling of aliphatic aziridines with indole, indoline, tetrahydroquinoline, and aniline has been developed to furnish the corresponding β-arylethylamine derivatives. The substrate scope was very general, and the protocol was also tolerated in the presence of various external additives. Control experiments suggested that the C-H cleavage step is the rate-determining step.

UR - http://hdl.handle.net/10754/676278

UR - https://pubs.acs.org/doi/10.1021/acs.orglett.2c00120

U2 - 10.1021/acs.orglett.2c00120

DO - 10.1021/acs.orglett.2c00120

M3 - Article

C2 - 35394290

SN - 1523-7060

JO - Organic Letters

JF - Organic Letters

ER -

Directing Group Guided Site-Selective Diversification of Indoles by Aziridine: Synthesis of β-Indolylethylamines

Abstract

Bibliographical note

ASJC Scopus subject areas

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