Copper-Catalyzed Radical Hydrazono-Phosphorylation of Alkenes.

Autor:	Ogundipe OO; Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University, 199 Renai Street, Suzhou, Jiangsu 215123, China., Shoberu A; Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University, 199 Renai Street, Suzhou, Jiangsu 215123, China., Xiao M; Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University, 199 Renai Street, Suzhou, Jiangsu 215123, China., Zou JP; Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University, 199 Renai Street, Suzhou, Jiangsu 215123, China.
Jazyk:	angličtina
Zdroj:	The Journal of organic chemistry [J Org Chem] 2022 Dec 02; Vol. 87 (23), pp. 15820-15829. Date of Electronic Publication: 2022 Nov 14.
DOI:	10.1021/acs.joc.2c01832
Abstrakt:	An efficient copper-catalyzed radical hydrazono-phosphorylation of alkenes with hydrazine derivatives and diarylphosphine oxides is described. The reaction provides a general and convenient method toward the synthesis of diverse β-hydrazonophosphine oxides in satisfactory yields. Based on conducted mechanistic experiments, a mechanism involving Ag-catalyzed oxidative generation of phosphinoyl radicals and subsequent addition to alkenes followed by Cu-assisted hydrazonation is proposed. Moreover, the practicability of the reaction is successfully demonstrated by its successful application on a gram scale.
Databáze:	MEDLINE
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