Metal-free oxidative hydrophosphinylation of 1,7-enynes

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

doi:10.1039/c5qo00430f

Metal-free oxidative hydrophosphinylation of 1,7-enynes

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

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Abstract

A new metal-free oxidative hydrophosphinylation of 1,7-enynes for forming polyfunctionalized 3,4-dihydroquinolin-2(1H)-ones has been realized using readily accessible diarylphosphine oxide and TBPB as an oxidant. The reaction pathway involves an in situ-generated P-centered radical-triggered α,β-conjugate addition/6-exo-dig cyclization/H-abstraction sequence, providing a direct and promising protocol for the formation of C-P, C-C and C-H bonds and rapid construction of complex heterocyclic compounds.

Original language	English
Pages (from-to)	385-393
Number of pages	9
Journal	Organic Chemistry Frontiers
Volume	3
Issue number	3
DOIs	https://doi.org/10.1039/c5qo00430f
State	Published - Mar 2016

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title = "Metal-free oxidative hydrophosphinylation of 1,7-enynes",

abstract = "A new metal-free oxidative hydrophosphinylation of 1,7-enynes for forming polyfunctionalized 3,4-dihydroquinolin-2(1H)-ones has been realized using readily accessible diarylphosphine oxide and TBPB as an oxidant. The reaction pathway involves an in situ-generated P-centered radical-triggered α,β-conjugate addition/6-exo-dig cyclization/H-abstraction sequence, providing a direct and promising protocol for the formation of C-P, C-C and C-H bonds and rapid construction of complex heterocyclic compounds.",

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

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year = "2016",

month = mar,

doi = "10.1039/c5qo00430f",

language = "英语",

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T1 - Metal-free oxidative hydrophosphinylation of 1,7-enynes

AU - Zhu, Yi Long

AU - Wang, De Cai

AU - Jiang, Bo

AU - Hao, Wen Juan

AU - Wei, Ping

AU - Wang, Ai Fang

AU - Qiu, Jiang Kai

AU - Tu, Shu Jiang

PY - 2016/3

Y1 - 2016/3

N2 - A new metal-free oxidative hydrophosphinylation of 1,7-enynes for forming polyfunctionalized 3,4-dihydroquinolin-2(1H)-ones has been realized using readily accessible diarylphosphine oxide and TBPB as an oxidant. The reaction pathway involves an in situ-generated P-centered radical-triggered α,β-conjugate addition/6-exo-dig cyclization/H-abstraction sequence, providing a direct and promising protocol for the formation of C-P, C-C and C-H bonds and rapid construction of complex heterocyclic compounds.

AB - A new metal-free oxidative hydrophosphinylation of 1,7-enynes for forming polyfunctionalized 3,4-dihydroquinolin-2(1H)-ones has been realized using readily accessible diarylphosphine oxide and TBPB as an oxidant. The reaction pathway involves an in situ-generated P-centered radical-triggered α,β-conjugate addition/6-exo-dig cyclization/H-abstraction sequence, providing a direct and promising protocol for the formation of C-P, C-C and C-H bonds and rapid construction of complex heterocyclic compounds.

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U2 - 10.1039/c5qo00430f

DO - 10.1039/c5qo00430f

M3 - 文章

AN - SCOPUS:84959019608

SN - 2052-4110

VL - 3

SP - 385

EP - 393

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 3

ER -

Metal-free oxidative hydrophosphinylation of 1,7-enynes

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