Rhodium(I)-Catalyzed Carboxylation of Aryl- and Alkenylboronic Esters with CO2

Kazutoshi Ukai, Masao Aoki, Jun Takaya, and Nobuharu Iwasawa*
Department of Chemistry, Tokyo Institute of Technology, O-Okayama, Meguro-ku, Tokyo 152-8551, Japan
J. Am. Chem. Soc., 2006, 128 (27), pp 8706–8707
DOI: 10.1021/ja061232m
Publication Date (Web): June 15, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, niwasawa@chem.titech.ac.jp

Abstract

Abstract Image

When the esters of arylboronic acids with 2,2-dimethylpropan-1,3-diol were treated with a catalytic amount of [Rh(OH)(cod)]2 in the presence of 1,3-bis(diphenylphosphino)propane and CsF in dioxane at 60 °C under carbon dioxide atmosphere, the benzoic acid derivatives were obtained in good yields. Reactions of alkenylboronic esters also proceeded under similar conditions to give α,β-unsaturated carboxylic acids. As these boronic esters are now easily available through coupling or direct borylation reactions, this method would be a useful method for the preparation of various functionalized aryl- and alkenyl-carboxylic acids.

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History

  • Published In Issue July 12, 2006
  • Received February 21, 2006

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