Jump to main content
Jump to site search


Synthesis of functionalized alkyl substituted benzoquinones by Rh-catalyzed additions of boronic acids

Author affiliations

Abstract

A general synthetic route to γ-oxo alkyl or α-hydroxy benzyl 2-substituted benzoquinones has been developed through a one-pot Rh-catalyzed C–C bond formation/oxidative demethylation sequence from 2,5-dimethoxy aryl boronic acids and several electron deficient alkenes or aldehydes. The process allows rapid access to functionalized benzoquinones under very mild conditions and good yields. We disclose the first example of a Rh-catalyzed 1,4-addition reaction of benzoquinonyl boronic acid to methyl vinyl ketone and other conjugate acceptors, which allows the direct synthesis of 2-(γ-functionalized alkyl) substituted benzoquinones.

Graphical abstract: Synthesis of functionalized alkyl substituted benzoquinones by Rh-catalyzed additions of boronic acids

Back to tab navigation

Supplementary files

Publication details

The article was received on 21 Apr 2017, accepted on 06 Jun 2017 and first published on 07 Jun 2017


Article type: Paper
DOI: 10.1039/C7OB00979H
Citation: Org. Biomol. Chem., 2017, Advance Article
  •   Request permissions

    Synthesis of functionalized alkyl substituted benzoquinones by Rh-catalyzed additions of boronic acids

    M. Veguillas, J. Rojas-Martín, M. Ribagorda and M. C. Carreño, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB00979H

Search articles by author

Spotlight

Advertisements