Synthesis of Tribenzo[b,e,g]phosphindole Oxides via Radical Bicyclization Cascades of o-Arylalkynylanilines

Jie Li; Wen Wen Zhang; Xiao Jing Wei; Wen Juan Hao; Guigen Li; Shu Jiang Tu; Bo Jiang

doi:10.1021/acs.orglett.7b02071

Synthesis of Tribenzo[b,e,g]phosphindole Oxides via Radical Bicyclization Cascades of o-Arylalkynylanilines

Jie Li, Wen Wen Zhang, Xiao Jing Wei, Wen Juan Hao, Guigen Li, Shu Jiang Tu, Bo Jiang

Chemistry and Biochemistry

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

20 Scopus citations

Abstract

A new DTBP/Mg(NO₃)₂-mediated bicyclization cascade of o-arylalkynylanilines with secondary arylphosphine oxides has been developed, enabling dual C(sp²)-H functionalization along with the cleavage of the C-N bond. The combination between regioselective P-centered radical-triggered [3 + 2] cyclization and C-centered radical-induced cross-coupling in a one-pot manner delivered 27 examples of tribenzo[b,e,g]phosphindole oxides with generally high regioselectivity. A reasonable mechanism for forming such products involving radical addition-cyclization cascade is proposed.

Original language	English
Pages (from-to)	4512-4515
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.7b02071
State	Published - Sep 1 2017

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title = "Synthesis of Tribenzo[b,e,g]phosphindole Oxides via Radical Bicyclization Cascades of o-Arylalkynylanilines",

abstract = "A new DTBP/Mg(NO3)2-mediated bicyclization cascade of o-arylalkynylanilines with secondary arylphosphine oxides has been developed, enabling dual C(sp2)-H functionalization along with the cleavage of the C-N bond. The combination between regioselective P-centered radical-triggered [3 + 2] cyclization and C-centered radical-induced cross-coupling in a one-pot manner delivered 27 examples of tribenzo[b,e,g]phosphindole oxides with generally high regioselectivity. A reasonable mechanism for forming such products involving radical addition-cyclization cascade is proposed.",

author = "Jie Li and Zhang, {Wen Wen} and Wei, {Xiao Jing} and Hao, {Wen Juan} and Guigen Li and Tu, {Shu Jiang} and Bo Jiang",

year = "2017",

month = sep,

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doi = "10.1021/acs.orglett.7b02071",

language = "English",

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T1 - Synthesis of Tribenzo[b,e,g]phosphindole Oxides via Radical Bicyclization Cascades of o-Arylalkynylanilines

AU - Li, Jie

AU - Zhang, Wen Wen

AU - Wei, Xiao Jing

AU - Hao, Wen Juan

AU - Li, Guigen

AU - Tu, Shu Jiang

AU - Jiang, Bo

PY - 2017/9/1

Y1 - 2017/9/1

N2 - A new DTBP/Mg(NO3)2-mediated bicyclization cascade of o-arylalkynylanilines with secondary arylphosphine oxides has been developed, enabling dual C(sp2)-H functionalization along with the cleavage of the C-N bond. The combination between regioselective P-centered radical-triggered [3 + 2] cyclization and C-centered radical-induced cross-coupling in a one-pot manner delivered 27 examples of tribenzo[b,e,g]phosphindole oxides with generally high regioselectivity. A reasonable mechanism for forming such products involving radical addition-cyclization cascade is proposed.

AB - A new DTBP/Mg(NO3)2-mediated bicyclization cascade of o-arylalkynylanilines with secondary arylphosphine oxides has been developed, enabling dual C(sp2)-H functionalization along with the cleavage of the C-N bond. The combination between regioselective P-centered radical-triggered [3 + 2] cyclization and C-centered radical-induced cross-coupling in a one-pot manner delivered 27 examples of tribenzo[b,e,g]phosphindole oxides with generally high regioselectivity. A reasonable mechanism for forming such products involving radical addition-cyclization cascade is proposed.

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