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

Catalysis Research Center

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

7 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

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Physical and Theoretical Chemistry

Access to Document

10.1021/acs.orglett.2c00120

Cite this

@article{646ba1a1c1504cc783534e23670d30af,

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",

year = "2022",

month = apr,

day = "8",

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

language = "English (US)",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

}

TY - JOUR

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

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this