Regioselective Synthesis of 2-Vinylanilines Using O-aroyloxycarba-mates by Sequential Decarboxylation/Amination/Heck Reaction

Peihe Li; Nuannuan Ma; Jikun Li; Zheng Wang; Qipu Dai; Changwen Hu

doi:10.1021/acs.joc.7b01020

Regioselective Synthesis of 2-Vinylanilines Using O-aroyloxycarba-mates by Sequential Decarboxylation/Amination/Heck Reaction

Peihe Li, Nuannuan Ma, Jikun Li, Zheng Wang, Qipu Dai^*, Changwen Hu

^*此作品的通讯作者

化学与化工学院

Beijing Institute of Technology

科研成果: 期刊稿件 › 文章 › 同行评审

13 引用（Scopus）

摘要

A new sequential approach for 2-vinylanilines utilizing aryl carboxylic acids as stable, inexpensive and widely available arylating reagents is described. Employing a Pd-POVs catalyst system, this protocol is not only overcoming the restriction barrier of decarboxylative coupling to ortho-substituted substrates, but also provides site-special to create new C(sp²)-N and C(sp²)-C(sp²) bonds. Mechanistic experiments suggest the cleavage of C(sp²)-COOH gives priority to C(sp²)-X bond in this reaction.

源语言	英语
页（从-至）	8251-8257
页数	7
期刊	Journal of Organic Chemistry
卷	82
期	15
DOI	https://doi.org/10.1021/acs.joc.7b01020
出版状态	已出版 - 4 8月 2017

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abstract = "A new sequential approach for 2-vinylanilines utilizing aryl carboxylic acids as stable, inexpensive and widely available arylating reagents is described. Employing a Pd-POVs catalyst system, this protocol is not only overcoming the restriction barrier of decarboxylative coupling to ortho-substituted substrates, but also provides site-special to create new C(sp2)-N and C(sp2)-C(sp2) bonds. Mechanistic experiments suggest the cleavage of C(sp2)-COOH gives priority to C(sp2)-X bond in this reaction.",

author = "Peihe Li and Nuannuan Ma and Jikun Li and Zheng Wang and Qipu Dai and Changwen Hu",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

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doi = "10.1021/acs.joc.7b01020",

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T1 - Regioselective Synthesis of 2-Vinylanilines Using O-aroyloxycarba-mates by Sequential Decarboxylation/Amination/Heck Reaction

AU - Li, Peihe

AU - Ma, Nuannuan

AU - Li, Jikun

AU - Wang, Zheng

AU - Dai, Qipu

AU - Hu, Changwen

PY - 2017/8/4

Y1 - 2017/8/4

N2 - A new sequential approach for 2-vinylanilines utilizing aryl carboxylic acids as stable, inexpensive and widely available arylating reagents is described. Employing a Pd-POVs catalyst system, this protocol is not only overcoming the restriction barrier of decarboxylative coupling to ortho-substituted substrates, but also provides site-special to create new C(sp2)-N and C(sp2)-C(sp2) bonds. Mechanistic experiments suggest the cleavage of C(sp2)-COOH gives priority to C(sp2)-X bond in this reaction.

AB - A new sequential approach for 2-vinylanilines utilizing aryl carboxylic acids as stable, inexpensive and widely available arylating reagents is described. Employing a Pd-POVs catalyst system, this protocol is not only overcoming the restriction barrier of decarboxylative coupling to ortho-substituted substrates, but also provides site-special to create new C(sp2)-N and C(sp2)-C(sp2) bonds. Mechanistic experiments suggest the cleavage of C(sp2)-COOH gives priority to C(sp2)-X bond in this reaction.

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SN - 0022-3263

VL - 82

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 15

ER -

Regioselective Synthesis of 2-Vinylanilines Using O-aroyloxycarba-mates by Sequential Decarboxylation/Amination/Heck Reaction

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