Synergistic palladium/copper-catalyzed Csp-Csp cross-couplings using aldehydes as latent α-alkoxyalkyl anion equivalents.

Chem Commun (Camb)

Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.

Published: June 2018

AI Article Synopsis

  • Researchers successfully developed a new method for Csp3-Csp2 cross-coupling, utilizing aldehydes as α-alkoxyalkyl anion equivalents.
  • The reaction, which is catalyzed by both palladium and copper, combines aromatic aldehydes and aryl bromides with silylboronates to produce silyl-protected benzhydrol derivatives.
  • The process involves creating a nucleophilic α-silyloxybenzylcopper(i) species that then undergoes palladium-catalyzed cross-coupling with aryl bromides.

Article Abstract

The first Csp3-Csp2 cross-coupling using aldehydes as latent α-alkoxyalkyl anion equivalents has been achieved. The synergistic palladium/copper-catalyzed reaction of aromatic aldehydes and aryl bromides with a silylboronate afforded the three-component coupling products, silyl-protected benzhydrol derivatives. The reaction pathway involves the catalytic formation of a nucleophilic α-silyloxybenzylcopper(i) species followed by its palladium-catalyzed cross-coupling with aryl bromides.

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http://dx.doi.org/10.1039/c8cc01055bDOI Listing

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Synergistic palladium/copper-catalyzed Csp-Csp cross-couplings using aldehydes as latent α-alkoxyalkyl anion equivalents.

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Article Synopsis
  • Researchers successfully developed a new method for Csp3-Csp2 cross-coupling, utilizing aldehydes as α-alkoxyalkyl anion equivalents.
  • The reaction, which is catalyzed by both palladium and copper, combines aromatic aldehydes and aryl bromides with silylboronates to produce silyl-protected benzhydrol derivatives.
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