Electrosynthesis of Phosphacycles via Dehydrogenative C–P Bond Formation Using DABCO as a Mediator | Zendy

Yuji Kurimoto | Zendy; Jun Yamashita | Zendy; Koichi Mitsudo | Zendy; Eisuke F. Sato | Zendy; Seiji Suga | Zendy

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

Author(s) -

Yuji Kurimoto,

Jun Yamashita,

Koichi Mitsudo,

Eisuke F. Sato,

Seiji Suga

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.1c00807

Subject(s) - chemistry , dabco , electrosynthesis , mediator , electrochemistry , combinatorial chemistry , hydrogen bond , hydrogen atom , molecule , octane , stereochemistry , medicinal chemistry , organic chemistry , group (periodic table) , medicine , electrode

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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