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TfOH-Catalyzed Phosphinylation of 2,3-Allenols into γ-Ketophosphine Oxides. | LitMetric

TfOH-Catalyzed Phosphinylation of 2,3-Allenols into γ-Ketophosphine Oxides.

J Org Chem

Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005 Fujian, China.

Published: June 2020

The first facile and efficient acid-catalyzed direct coupling of a wide range of unprotected 2,3-allenols with arylphosphine oxides was developed, offering a general, one-step approach for the synthesis of structurally diverse γ-ketophosphine oxides accompanied by concurrent C-P/C═O bond formation with remarkable functional group tolerance and complete atom-economy under metal- and additive-free conditions. Mechanistic studies showed that this transformation involved a rearrangement and a phospha-Michael reaction.

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http://dx.doi.org/10.1021/acs.joc.0c00328DOI Listing

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