Pd-Catalyzed Dearomative Three-Component Reaction of Bromoarenes with Diazo Compounds and Allylborates

Masaaki Komatsuda; Hiroki Kato; Kei Muto; Junichiro Yamaguchi

doi:10.1021/acscatal.9b03461

Pd-Catalyzed Dearomative Three-Component Reaction of Bromoarenes with Diazo Compounds and Allylborates

Masaaki Komatsuda, Hiroki Kato, Kei Muto^*, Junichiro Yamaguchi

^*Corresponding author for this work

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

30 Citations (Scopus)

Abstract

A catalytic dearomative three-component reaction of bromoarenes with TMS-diazomethane and allyl borate was developed. The key of this assembling reaction is the use of a diazo compound to generate a Pd-π-benzyl intermediate through a Pd-carbene species. This method allowed for a dearomative functionalization, using arenes as limiting reagents. Heteroaryl bromides were also applicable to give dearomatized structures under the reaction conditions.

Original language	English
Pages (from-to)	8991-8995
Number of pages	5
Journal	ACS Catalysis
Volume	9
Issue number	10
DOIs	https://doi.org/10.1021/acscatal.9b03461
Publication status	Published - 2019 Oct 4

Keywords

(Hetero)arenes
Alicyclic compounds
Dearomatization
Diazo compounds
Palladium

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1021/acscatal.9b03461

Cite this

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title = "Pd-Catalyzed Dearomative Three-Component Reaction of Bromoarenes with Diazo Compounds and Allylborates",

abstract = "A catalytic dearomative three-component reaction of bromoarenes with TMS-diazomethane and allyl borate was developed. The key of this assembling reaction is the use of a diazo compound to generate a Pd-π-benzyl intermediate through a Pd-carbene species. This method allowed for a dearomative functionalization, using arenes as limiting reagents. Heteroaryl bromides were also applicable to give dearomatized structures under the reaction conditions.",

keywords = "(Hetero)arenes, Alicyclic compounds, Dearomatization, Diazo compounds, Palladium",

author = "Masaaki Komatsuda and Hiroki Kato and Kei Muto and Junichiro Yamaguchi",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Nos. JP19H02726 (to J.Y.), JP18H04661 (Hybrid Catalysis), and JP19K15573 (to K.M.). The Materials Characterization Central Laboratory in Waseda University is acknowledged for the support of HRMS measurement. We would like to thank National Institute of Health Sciences in Japan for the support of NMR measurement. Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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AU - Komatsuda, Masaaki

AU - Kato, Hiroki

AU - Muto, Kei

AU - Yamaguchi, Junichiro

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Nos. JP19H02726 (to J.Y.), JP18H04661 (Hybrid Catalysis), and JP19K15573 (to K.M.). The Materials Characterization Central Laboratory in Waseda University is acknowledged for the support of HRMS measurement. We would like to thank National Institute of Health Sciences in Japan for the support of NMR measurement. Publisher Copyright: © 2019 American Chemical Society.

PY - 2019/10/4

Y1 - 2019/10/4

N2 - A catalytic dearomative three-component reaction of bromoarenes with TMS-diazomethane and allyl borate was developed. The key of this assembling reaction is the use of a diazo compound to generate a Pd-π-benzyl intermediate through a Pd-carbene species. This method allowed for a dearomative functionalization, using arenes as limiting reagents. Heteroaryl bromides were also applicable to give dearomatized structures under the reaction conditions.

AB - A catalytic dearomative three-component reaction of bromoarenes with TMS-diazomethane and allyl borate was developed. The key of this assembling reaction is the use of a diazo compound to generate a Pd-π-benzyl intermediate through a Pd-carbene species. This method allowed for a dearomative functionalization, using arenes as limiting reagents. Heteroaryl bromides were also applicable to give dearomatized structures under the reaction conditions.

KW - (Hetero)arenes

KW - Alicyclic compounds

KW - Dearomatization

KW - Diazo compounds

KW - Palladium

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Pd-Catalyzed Dearomative Three-Component Reaction of Bromoarenes with Diazo Compounds and Allylborates

Abstract

Keywords

ASJC Scopus subject areas

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