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Synfacts 2022; 18(07): 0747
DOI: 10.1055/s-0041-1737632
Metals in Synthesis

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

Authors

    Contributor(s):

  • Martin Oestreich

  • Hendrik F. T. Klare

  • Phillip Pommerening

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
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Key words

γ-boryl esters - boration - carbonylative catenation - copper catalysis - styrenes

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.


 

 

Publication History

Article published online:
15 June 2022

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