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

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

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

14 Citations (Scopus)

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.

Original language	English
Pages (from-to)	8251-8257
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	82
Issue number	15
DOIs	https://doi.org/10.1021/acs.joc.7b01020
Publication status	Published - 4 Aug 2017

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Li, P., Ma, N., Li, J., Wang, Z., Dai, Q., & Hu, C. (2017). Regioselective Synthesis of 2-Vinylanilines Using O-aroyloxycarba-mates by Sequential Decarboxylation/Amination/Heck Reaction. Journal of Organic Chemistry, 82(15), 8251-8257. https://doi.org/10.1021/acs.joc.7b01020

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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.",

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

Abstract

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