Transition metal-free phosphonocarboxylation of alkenes with carbon dioxide via visible-light photoredox catalysis

Qiang Fu, Zhi-Yu Bo, Jian-Heng Ye, Tao Ju, He Huang, Li-Li Liao and Da-Gang Yu ()
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Qiang Fu: Sichuan University
Zhi-Yu Bo: Sichuan University
Jian-Heng Ye: Sichuan University
Tao Ju: Sichuan University
He Huang: Sichuan University
Li-Li Liao: Sichuan University
Da-Gang Yu: Sichuan University

Nature Communications, 2019, vol. 10, issue 1, 1-9

Abstract: Abstract Catalytic difunctionalization of alkenes has been an ideal strategy to generate structurally complex molecules with diverse substitution patterns. Although both phosphonyl and carboxyl groups are valuable functional groups, the simultaneous incorporation of them via catalytic difunctionalization of alkenes, ideally from abundant, inexpensive and easy-to-handle raw materials, has not been realized. Herein, we report the phosphonocarboxylation of alkenes with CO2 via visible-light photoredox catalysis. This strategy is sustainable, general and practical, providing facile access to important β-phosphono carboxylic acids, including structurally complex unnatural α-amino acids. Diverse alkenes, including enamides, styrenes, enolsilanes and acrylates, undergo such reactions efficiently under mild reaction conditions. Moreover, this method represents a rare example of redox-neutral difunctionalization of alkenes with H-P(O) compounds, including diaryl- and dialkyl- phosphine oxides and phosphites. Importantly, these transition-metal-free reactions also feature low catalyst loading, high regio- and chemo-selectivities, good functional group tolerance, easy scalability and potential for product derivatization.

Date: 2019
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DOI: 10.1038/s41467-019-11528-8

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