Copper-Catalyzed Electrophilic Enamidation Using Dioxazolones through Hydrozirconation of Alkynes

Shona Banjo; Keisuke Nakata; Eiko Nakasuji; Soichiro Yasui; Noritaka Chida; Takaaki Sato

doi:10.1021/acs.orglett.2c03497

Copper-Catalyzed Electrophilic Enamidation Using Dioxazolones through Hydrozirconation of Alkynes

Shona Banjo, Keisuke Nakata, Eiko Nakasuji, Soichiro Yasui, Noritaka Chida, Takaaki Sato

Department of Applied Chemistry

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

3 Citations (Scopus)

Abstract

A copper-catalyzed electrophilic enamidation starting from alkynes is reported. Hydrozirconation of an alkyne with the Schwartz reagent forms a vinyl zirconium intermediate, which directly undergoes a copper-catalyzed electrophilic enamidation with dioxazolones. High functional group tolerance of hydrozirconation enables the use of functionalized alkynes including esters. The developed conditions are successfully applied to syntheses of partial structures found in biologically active natural products.

Original language	English
Pages (from-to)	8662-8666
Number of pages	5
Journal	Organic Letters
Volume	24
Issue number	47
DOIs	https://doi.org/10.1021/acs.orglett.2c03497
Publication status	Published - 2022 Dec 2

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.2c03497

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title = "Copper-Catalyzed Electrophilic Enamidation Using Dioxazolones through Hydrozirconation of Alkynes",

abstract = "A copper-catalyzed electrophilic enamidation starting from alkynes is reported. Hydrozirconation of an alkyne with the Schwartz reagent forms a vinyl zirconium intermediate, which directly undergoes a copper-catalyzed electrophilic enamidation with dioxazolones. High functional group tolerance of hydrozirconation enables the use of functionalized alkynes including esters. The developed conditions are successfully applied to syntheses of partial structures found in biologically active natural products.",

author = "Shona Banjo and Keisuke Nakata and Eiko Nakasuji and Soichiro Yasui and Noritaka Chida and Takaaki Sato",

note = "Funding Information: This research was supported by a Grant-in-Aid for Scientific Research (C) from Ministry of Education, Culture, Sports, Science and Technology (MEXT) (15K05436). The authors thank Prof. Yukari Fujimoto and Prof. Takanori Matsumaru, Keio University, for helping to measure ESI–MS. Publisher Copyright: {\textcopyright} 2022 American Chemical Society.",

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T1 - Copper-Catalyzed Electrophilic Enamidation Using Dioxazolones through Hydrozirconation of Alkynes

AU - Banjo, Shona

AU - Nakata, Keisuke

AU - Nakasuji, Eiko

AU - Yasui, Soichiro

AU - Chida, Noritaka

AU - Sato, Takaaki

N1 - Funding Information: This research was supported by a Grant-in-Aid for Scientific Research (C) from Ministry of Education, Culture, Sports, Science and Technology (MEXT) (15K05436). The authors thank Prof. Yukari Fujimoto and Prof. Takanori Matsumaru, Keio University, for helping to measure ESI–MS. Publisher Copyright: © 2022 American Chemical Society.

PY - 2022/12/2

Y1 - 2022/12/2

N2 - A copper-catalyzed electrophilic enamidation starting from alkynes is reported. Hydrozirconation of an alkyne with the Schwartz reagent forms a vinyl zirconium intermediate, which directly undergoes a copper-catalyzed electrophilic enamidation with dioxazolones. High functional group tolerance of hydrozirconation enables the use of functionalized alkynes including esters. The developed conditions are successfully applied to syntheses of partial structures found in biologically active natural products.

AB - A copper-catalyzed electrophilic enamidation starting from alkynes is reported. Hydrozirconation of an alkyne with the Schwartz reagent forms a vinyl zirconium intermediate, which directly undergoes a copper-catalyzed electrophilic enamidation with dioxazolones. High functional group tolerance of hydrozirconation enables the use of functionalized alkynes including esters. The developed conditions are successfully applied to syntheses of partial structures found in biologically active natural products.

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JO - Organic Letters

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Copper-Catalyzed Electrophilic Enamidation Using Dioxazolones through Hydrozirconation of Alkynes

Abstract

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