Electrosynthesis of Phosphacycles via Dehydrogenative C-P Bond Formation Using DABCO as a Mediator

Yuji Kurimoto; Jun Yamashita; Koichi Mitsudo; Eisuke Sato; Seiji Suga

doi:10.1021/acs.orglett.1c00807

Electrosynthesis of Phosphacycles via Dehydrogenative C-P Bond Formation Using DABCO as a Mediator

Yuji Kurimoto, Jun Yamashita, Koichi Mitsudo, Eisuke Sato, Seiji Suga

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

16 Citations (Scopus)

Abstract

The first electrochemical synthesis of diarylphosphole oxides (DPOs) was achieved under mild conditions. The practical protocol employs commercially available and inexpensive DABCO as a hydrogen atom transfer (HAT) mediator, leading to various DPOs in moderate to good yields. This procedure can also be applied to the synthesis of six-membered phosphacycles, such as phenophosphazine derivatives. Mechanistic studies suggested that the reaction proceeds via an electro-generated phosphinyl radical.

Original language	English
Pages (from-to)	3120-3124
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.1c00807
Publication status	Published - Apr 16 2021

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "The first electrochemical synthesis of diarylphosphole oxides (DPOs) was achieved under mild conditions. The practical protocol employs commercially available and inexpensive DABCO as a hydrogen atom transfer (HAT) mediator, leading to various DPOs in moderate to good yields. This procedure can also be applied to the synthesis of six-membered phosphacycles, such as phenophosphazine derivatives. Mechanistic studies suggested that the reaction proceeds via an electro-generated phosphinyl radical. ",

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AU - Kurimoto, Yuji

AU - Yamashita, Jun

AU - Mitsudo, Koichi

AU - Sato, Eisuke

AU - Suga, Seiji

N1 - Funding Information: This work was supported in part by JSPS KAKENHI Grants JP18J21360, JP19K05477, JP19K05478, and JP18H04455 in Middle Molecular Strategy. Publisher Copyright: © 2021 American Chemical Society.

PY - 2021/4/16

Y1 - 2021/4/16

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AB - The first electrochemical synthesis of diarylphosphole oxides (DPOs) was achieved under mild conditions. The practical protocol employs commercially available and inexpensive DABCO as a hydrogen atom transfer (HAT) mediator, leading to various DPOs in moderate to good yields. This procedure can also be applied to the synthesis of six-membered phosphacycles, such as phenophosphazine derivatives. Mechanistic studies suggested that the reaction proceeds via an electro-generated phosphinyl radical.

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Electrosynthesis of Phosphacycles via Dehydrogenative C-P Bond Formation Using DABCO as a Mediator

Abstract

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