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Synfacts | Synfact of the month 2022-07-19

Take Two CO: Access to γ-Boryl Esters by Boration and Carbonylative Catenation of Styrenes in One Pot

Contributors: Martin Oestreich, Hendrik F. T. Klare, Phillip Pommerening

Significance

A copper-catalyzed carbonylative four-component coupling of olefins to access γ-boryl esters is disclosed. Two CO molecules act as the –CH2CO– source. The regio- and syn-selective boryl cupration gives the products in high stereoselectivity.

Comment

Based on 13C and 2H NMR labeling experiments, the shown mechanism is proposed. Further synthetic transformations of the γ-boryl esters were performed to demonstrate the synthetic utility of this protocol.

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Wu F.-P, Yang Y, Fuentes DP, Wu X.-F. * Leibniz-Institut für Katalyse e.V., Rostock, Germany and Dalian Institute of Chemical Physics, Liaoning, P. R. of China

Copper-Catalyzed Carbonylative Catenation of Olefins: Direct Synthesis of γ-Boryl Esters
Chem. 2022, DOI: 10.1016/j.chempr.2022.03.013