Photoredox-Catalyzed Phosphonocarboxylation of Allenes with Phosphine Oxides and CO.

J Org Chem

Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361001, Fujian, People's Republic of China.

Published: October 2023

Phosphonocarboxylation of allenes with diarylphosphine oxides and CO via visible-light photoredox catalysis was developed for the first time. This work provided practical and sustainable access to highly valuable but otherwise difficult-to-access linear allylic β-phosphonyl carboxylic acids in moderate yields with exclusive regio- and stereoselectivity. This method was also characterized by step and atom economy and transition-metal free and mild conditions. Preliminary mechanistic studies suggested that allyl-methyl carbanion species are the key intermediates.

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http://dx.doi.org/10.1021/acs.joc.3c01583DOI Listing

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Photoredox-Catalyzed Phosphonocarboxylation of Allenes with Phosphine Oxides and CO.

J Org Chem

October 2023

Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361001, Fujian, People's Republic of China.

Phosphonocarboxylation of allenes with diarylphosphine oxides and CO via visible-light photoredox catalysis was developed for the first time. This work provided practical and sustainable access to highly valuable but otherwise difficult-to-access linear allylic β-phosphonyl carboxylic acids in moderate yields with exclusive regio- and stereoselectivity. This method was also characterized by step and atom economy and transition-metal free and mild conditions.

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