Catalytic Diazosulfonylation of Enynals toward Diazoindenes via
Oxidative Radical-Triggered 5-exo-trig Carbocyclizations

Wen-Juan Hao; Yan Du; Dan Wang; Bo Jiang; Qian Gao; Shu-Jiang Tu; Guigen Li

Catalytic Diazosulfonylation of Enynals toward Diazoindenes via Oxidative Radical-Triggered 5-exo-trig Carbocyclizations

Wen-Juan Hao, Yan Du, Dan Wang, Bo Jiang, Qian Gao, Shu-Jiang Tu, Guigen Li

Chemistry and Biochemistry

Research output: Contribution to journal › Article

Abstract

Catalytic diazosulfonylation of enynals with arylsulfonyl hydrazides has been established by using tert-butyl hydroperoxide (TBHP) as the oxidant with tetrabutylammonium iodide (TBAI) under a convenient system. The reaction occurred through oxidative radical triggered S-exo-trig carbocyclization cascading to afford sulfonylated diazoindenes regioselectively. The new diazosulfonylation reaction features a broad substrate scope, readily accessible starting materials, and a simple one-pot process.

Original language	English
Pages (from-to)	1884-1887
Journal	Organic Letters
State	Published - Apr 2016

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@article{d7158466d66f4dd283b9da7cfc8617d7,

title = "Catalytic Diazosulfonylation of Enynals toward Diazoindenes via Oxidative Radical-Triggered 5-exo-trig Carbocyclizations",

abstract = "Catalytic diazosulfonylation of enynals with arylsulfonyl hydrazides has been established by using tert-butyl hydroperoxide (TBHP) as the oxidant with tetrabutylammonium iodide (TBAI) under a convenient system. The reaction occurred through oxidative radical triggered S-exo-trig carbocyclization cascading to afford sulfonylated diazoindenes regioselectively. The new diazosulfonylation reaction features a broad substrate scope, readily accessible starting materials, and a simple one-pot process.",

author = "Wen-Juan Hao and Yan Du and Dan Wang and Bo Jiang and Qian Gao and Shu-Jiang Tu and Guigen Li",

year = "2016",

month = apr,

language = "English",

pages = "1884--1887",

journal = "Organic Letters",

issn = "1523-7060",

}

TY - JOUR

T1 - Catalytic Diazosulfonylation of Enynals toward Diazoindenes via Oxidative Radical-Triggered 5-exo-trig Carbocyclizations

AU - Hao, Wen-Juan

AU - Du, Yan

AU - Wang, Dan

AU - Jiang, Bo

AU - Gao, Qian

AU - Tu, Shu-Jiang

AU - Li, Guigen

PY - 2016/4

Y1 - 2016/4

N2 - Catalytic diazosulfonylation of enynals with arylsulfonyl hydrazides has been established by using tert-butyl hydroperoxide (TBHP) as the oxidant with tetrabutylammonium iodide (TBAI) under a convenient system. The reaction occurred through oxidative radical triggered S-exo-trig carbocyclization cascading to afford sulfonylated diazoindenes regioselectively. The new diazosulfonylation reaction features a broad substrate scope, readily accessible starting materials, and a simple one-pot process.

AB - Catalytic diazosulfonylation of enynals with arylsulfonyl hydrazides has been established by using tert-butyl hydroperoxide (TBHP) as the oxidant with tetrabutylammonium iodide (TBAI) under a convenient system. The reaction occurred through oxidative radical triggered S-exo-trig carbocyclization cascading to afford sulfonylated diazoindenes regioselectively. The new diazosulfonylation reaction features a broad substrate scope, readily accessible starting materials, and a simple one-pot process.

M3 - Article

SP - 1884

EP - 1887

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

ER -