tBuOK-Promoted Cyclization of Imines with Aryl Halides

Ya Wei Li; Hong Xing Zheng; Bo Yang; Xiang Huan Shan; Jian Ping Qu; Yan Biao Kang

doi:10.1021/acs.orglett.0c01615

^tBuOK-Promoted Cyclization of Imines with Aryl Halides

Ya Wei Li, Hong Xing Zheng, Bo Yang, Xiang Huan Shan, Jian Ping Qu, Yan Biao Kang

School of Chemistry and Moleculai Engineering

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

11 Scopus citations

Abstract

A transition-metal-free indole synthesis using radical coupling of 2-halotoluenes and imines via the later-stage C-N bond construction was reported for the first time. It includes an aminyl radical generation by C-H cleaving addition of 2-halotoluenes to imines via the carbanion radical relay and an intramolecular coupling of aryl halides with aminyl radicals. One standard condition can be used for all halides including F, Cl, Br, and I. No extra oxidant or transition metal is required.

Original language	English
Pages (from-to)	4553-4556
Number of pages	4
Journal	Organic Letters
Volume	22
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.0c01615
State	Published - 5 Jun 2020

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title = "tBuOK-Promoted Cyclization of Imines with Aryl Halides",

abstract = "A transition-metal-free indole synthesis using radical coupling of 2-halotoluenes and imines via the later-stage C-N bond construction was reported for the first time. It includes an aminyl radical generation by C-H cleaving addition of 2-halotoluenes to imines via the carbanion radical relay and an intramolecular coupling of aryl halides with aminyl radicals. One standard condition can be used for all halides including F, Cl, Br, and I. No extra oxidant or transition metal is required.",

author = "Li, {Ya Wei} and Zheng, {Hong Xing} and Bo Yang and Shan, {Xiang Huan} and Qu, {Jian Ping} and Kang, {Yan Biao}",

note = "Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

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doi = "10.1021/acs.orglett.0c01615",

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T1 - tBuOK-Promoted Cyclization of Imines with Aryl Halides

AU - Li, Ya Wei

AU - Zheng, Hong Xing

AU - Yang, Bo

AU - Shan, Xiang Huan

AU - Qu, Jian Ping

AU - Kang, Yan Biao

PY - 2020/6/5

Y1 - 2020/6/5

N2 - A transition-metal-free indole synthesis using radical coupling of 2-halotoluenes and imines via the later-stage C-N bond construction was reported for the first time. It includes an aminyl radical generation by C-H cleaving addition of 2-halotoluenes to imines via the carbanion radical relay and an intramolecular coupling of aryl halides with aminyl radicals. One standard condition can be used for all halides including F, Cl, Br, and I. No extra oxidant or transition metal is required.

AB - A transition-metal-free indole synthesis using radical coupling of 2-halotoluenes and imines via the later-stage C-N bond construction was reported for the first time. It includes an aminyl radical generation by C-H cleaving addition of 2-halotoluenes to imines via the carbanion radical relay and an intramolecular coupling of aryl halides with aminyl radicals. One standard condition can be used for all halides including F, Cl, Br, and I. No extra oxidant or transition metal is required.

UR - http://www.scopus.com/inward/record.url?scp=85085768570&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.0c01615

DO - 10.1021/acs.orglett.0c01615

M3 - 文章

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AN - SCOPUS:85085768570

SN - 1523-7060

VL - 22

SP - 4553

EP - 4556

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

^tBuOK-Promoted Cyclization of Imines with Aryl Halides

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