Catalytic Arylsulfonyl Radical Triggered 1,7-Enyne Bicyclizations

Yi Long Zhu; Bo Jiang; Wen Juan Hao; Jiang Kai Qiu; Jun Sun; De Cai Wang; Ping Wei; Ai Fang Wang; Guigen Li; Shu Jiang Tu

doi:10.1021/acs.orglett.5b03100

Catalytic Arylsulfonyl Radical Triggered 1,7-Enyne Bicyclizations

Yi Long Zhu, Bo Jiang, Wen Juan Hao, Jiang Kai Qiu, Jun Sun, De Cai Wang, Ping Wei, Ai Fang Wang, Guigen Li, Shu Jiang Tu

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

114 Scopus citations

Abstract

A new metal-free bicyclization reaction of 1,7-enynes anchored by α,β-conjugates with arylsulfonyl radicals generated in situ from sulfonyl hydrazides has been established using tert-butyl hydroperoxide and tetrabutylammonium iodide. The reactions occurred through sulfonylation/6-exo-dig/6-exo-trig bicyclization/in situ desulfonylation/5-exo-trig cyclization/alkyl or alkenyl migration cascade mechanism to give benzo[j]phenanthridines regioselectively.

Original language	English
Pages (from-to)	6078-6081
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	24
DOIs	https://doi.org/10.1021/acs.orglett.5b03100
State	Published - 18 Dec 2015

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@article{b129a3cdcc404fe4bd1b21b20a4eb60d,

title = "Catalytic Arylsulfonyl Radical Triggered 1,7-Enyne Bicyclizations",

abstract = "A new metal-free bicyclization reaction of 1,7-enynes anchored by α,β-conjugates with arylsulfonyl radicals generated in situ from sulfonyl hydrazides has been established using tert-butyl hydroperoxide and tetrabutylammonium iodide. The reactions occurred through sulfonylation/6-exo-dig/6-exo-trig bicyclization/in situ desulfonylation/5-exo-trig cyclization/alkyl or alkenyl migration cascade mechanism to give benzo[j]phenanthridines regioselectively.",

author = "Zhu, {Yi Long} and Bo Jiang and Hao, {Wen Juan} and Qiu, {Jiang Kai} and Jun Sun and Wang, {De Cai} and Ping Wei and Wang, {Ai Fang} and Guigen Li and Tu, {Shu Jiang}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

month = dec,

day = "18",

doi = "10.1021/acs.orglett.5b03100",

language = "英语",

volume = "17",

pages = "6078--6081",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "24",

}

TY - JOUR

T1 - Catalytic Arylsulfonyl Radical Triggered 1,7-Enyne Bicyclizations

AU - Zhu, Yi Long

AU - Jiang, Bo

AU - Hao, Wen Juan

AU - Qiu, Jiang Kai

AU - Sun, Jun

AU - Wang, De Cai

AU - Wei, Ping

AU - Wang, Ai Fang

AU - Li, Guigen

AU - Tu, Shu Jiang

PY - 2015/12/18

Y1 - 2015/12/18

N2 - A new metal-free bicyclization reaction of 1,7-enynes anchored by α,β-conjugates with arylsulfonyl radicals generated in situ from sulfonyl hydrazides has been established using tert-butyl hydroperoxide and tetrabutylammonium iodide. The reactions occurred through sulfonylation/6-exo-dig/6-exo-trig bicyclization/in situ desulfonylation/5-exo-trig cyclization/alkyl or alkenyl migration cascade mechanism to give benzo[j]phenanthridines regioselectively.

AB - A new metal-free bicyclization reaction of 1,7-enynes anchored by α,β-conjugates with arylsulfonyl radicals generated in situ from sulfonyl hydrazides has been established using tert-butyl hydroperoxide and tetrabutylammonium iodide. The reactions occurred through sulfonylation/6-exo-dig/6-exo-trig bicyclization/in situ desulfonylation/5-exo-trig cyclization/alkyl or alkenyl migration cascade mechanism to give benzo[j]phenanthridines regioselectively.

UR - http://www.scopus.com/inward/record.url?scp=84952673943&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.5b03100

DO - 10.1021/acs.orglett.5b03100

M3 - 文章

C2 - 26618403

AN - SCOPUS:84952673943

SN - 1523-7060

VL - 17

SP - 6078

EP - 6081

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

Catalytic Arylsulfonyl Radical Triggered 1,7-Enyne Bicyclizations

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