Tunable synthesis of chalcophosphinic amides and tertiary phosphinates using tert-butyl N,N-dialkylperoxyamidate

Liu, Kun; Chang, Xuexue; He, Yimiao; Su, Zhongfu; Huang, Yanmin; Huang, Chusheng; Lei, Jian; Zhu, Qiang

doi:10.1039/d1qo00542a

Org. Chem. Front.

2021

DOI: 10.1039/d1qo00542a

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Tunable synthesis of chalcophosphinic amides and tertiary phosphinates using tert-butyl N,N-dialkylperoxyamidate

Kun Liu

Xuexue Chang

Yimiao He

et al.

Abstract: The tunable access of chalcophosphinic amides and phosphinates via copper-catalyzed reaction between phosphine chalcoxides and tert-butyl N, N-dialkylperoxyamidate has been developed. tert-Butyl N, N-dialkylperoxyamidate plays a dual role as a...

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Synthesis of Phosphinic Amides from Chlorophosphines and Hydroxyl Amines via P(III) to P(V) Rearrangement

Cheng

et al. 2023

Org. Lett.

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Phosphoranyl radicals are essential mediators to bring about new radicals but often produce a stoichiometric amount of phosphine oxide/sulfide waste. Herein, we devised a phosphorus-containing species as a radical precursor, but without the generation of phosphorus waste. Accordingly, a catalyst-free synthesis of phosphinic amides from hydroxyl amines and chlorophosphines via P(III) to P(V) rearrangement is described. Mechanistically, it may involve the initial formation of a R2N–O–PR2 species that undergoes homolysis of N–O bonds and subsequent radical recombination.

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Synthesis of Phosphinic Amides from Chlorophosphines and Hydroxyl Amines via P(III) to P(V) Rearrangement

Cheng

et al. 2023

Org. Lett.

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show abstract

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Tunable synthesis of chalcophosphinic amides and tertiary phosphinates using tert-butyl N,N-dialkylperoxyamidate

Abstract: The tunable access of chalcophosphinic amides and phosphinates via copper-catalyzed reaction between phosphine chalcoxides and tert-butyl N, N-dialkylperoxyamidate has been developed. tert-Butyl N, N-dialkylperoxyamidate plays a dual role as a...

Cited by 1 publication

References 38 publications

Synthesis of Phosphinic Amides from Chlorophosphines and Hydroxyl Amines via P(III) to P(V) Rearrangement

Synthesis of Phosphinic Amides from Chlorophosphines and Hydroxyl Amines via P(III) to P(V) Rearrangement

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