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Synlett 2011(17): 2517-2520  
DOI: 10.1055/s-0030-1260319
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium(I)-Catalyzed 1,4-Addition of Arylboronic Acids to Acrylic Acid in Water: One-Step Preparation of 3-Arylpropionic Acids

Nicolas R. Vautravers, Bernhard Breit*
Institut für Organische Chemie und Biochemie, Freiburg Institute for Advanced Studies (FRIAS), Albert-Ludwigs-Universität Freiburg, Albertstr. 21, 79104 Freiburg, Germany
Fax: +49(761)2038715; e-Mail: bernhard.breit@chemie.uni-freiburg.de;
Further Information

Publication History

Received 12 July 2011
Publication Date:
19 September 2011 (online)

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Abstract

A practical method for the one-step preparation of 3-arylpropionic acids through rhodium-catalyzed 1,4-addition of arylboronic acids to acrylic acid is reported. The method is applicable to a broad scope of aryl boronic acids and displays a wide functional group tolerance operating in water as the optimal reaction medium.

Key words

boronic acids - acrylic acid - water - conjugate addition - rhodium

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17

Slightly lower yields were obtained when non-degassed H2O was used.

18

Frost and co-workers reported the failure of the reaction between 1-naphthalene boronic acid and free α,β-unsaturated carboxylic acid with [Rh(COD)Cl]2 (see ref 3b). In our hands, the use of 2-naphthalene boronic acid in the presence of acrylic acid did not work with [Rh(COD)OH]2 either, which tends to prove the poor reactivity of naphthalene boronic acid derivatives when mixed together with free carboxylic acid under such conditions.