Pd-Catalyzed Dearomative Allylation of Benzyl Phosphates

Masaaki Komatsuda; Kei Muto; Junichiro Yamaguchi

doi:10.1021/acs.orglett.8b01807

Pd-Catalyzed Dearomative Allylation of Benzyl Phosphates

Masaaki Komatsuda, Kei Muto^*, Junichiro Yamaguchi

^*Corresponding author for this work

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

32 Citations (Scopus)

Abstract

Dearomative C-C bond formation of benzyl phosphates has been developed. In the presence of a palladium/PAr₃ catalyst, benzyl phosphates reacted with allyl borates to generate the allylated product in a dearomative fashion. The resulting dearomatized molecules were successfully derivatized by Simmons-Smith cyclopropanation and oxidation.

Original language	English
Pages (from-to)	4354-4357
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.8b01807
Publication status	Published - 2018 Jul 20

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b01807

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title = "Pd-Catalyzed Dearomative Allylation of Benzyl Phosphates",

abstract = "Dearomative C-C bond formation of benzyl phosphates has been developed. In the presence of a palladium/PAr3 catalyst, benzyl phosphates reacted with allyl borates to generate the allylated product in a dearomative fashion. The resulting dearomatized molecules were successfully derivatized by Simmons-Smith cyclopropanation and oxidation.",

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

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Nos. JP16H04148 (to J.Y.), JP17K14453, and JP18H04661 (to K.M.). The Materials Characterization Central Laboratory in Waseda University is acknowledged for HRMS measurements. We thank Prof. Seijiro Hosokawa for providing us with a melting point apparatus. Publisher Copyright: Copyright {\textcopyright} 2018 American Chemical Society.",

year = "2018",

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doi = "10.1021/acs.orglett.8b01807",

language = "English",

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journal = "Organic Letters",

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T1 - Pd-Catalyzed Dearomative Allylation of Benzyl Phosphates

AU - Komatsuda, Masaaki

AU - Muto, Kei

AU - Yamaguchi, Junichiro

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Nos. JP16H04148 (to J.Y.), JP17K14453, and JP18H04661 (to K.M.). The Materials Characterization Central Laboratory in Waseda University is acknowledged for HRMS measurements. We thank Prof. Seijiro Hosokawa for providing us with a melting point apparatus. Publisher Copyright: Copyright © 2018 American Chemical Society.

PY - 2018/7/20

Y1 - 2018/7/20

N2 - Dearomative C-C bond formation of benzyl phosphates has been developed. In the presence of a palladium/PAr3 catalyst, benzyl phosphates reacted with allyl borates to generate the allylated product in a dearomative fashion. The resulting dearomatized molecules were successfully derivatized by Simmons-Smith cyclopropanation and oxidation.

AB - Dearomative C-C bond formation of benzyl phosphates has been developed. In the presence of a palladium/PAr3 catalyst, benzyl phosphates reacted with allyl borates to generate the allylated product in a dearomative fashion. The resulting dearomatized molecules were successfully derivatized by Simmons-Smith cyclopropanation and oxidation.

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JO - Organic Letters

JF - Organic Letters

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ER -

Pd-Catalyzed Dearomative Allylation of Benzyl Phosphates

Abstract

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