Rhodium-Catalyzed Addition of Organoboronic Acids to Aldehydes

Masaaki Sakai; Masato Ueda; Norio Miyaura

doi:10.1002/(SICI)1521-3773(19981217)37:23<3279::AID-ANIE3279>3.0.CO;2-M

Rhodium-Catalyzed Addition of Organoboronic Acids to Aldehydes

Angew Chem Int Ed Engl. 1998 Dec 17;37(23):3279-3281. doi: 10.1002/(SICI)1521-3773(19981217)37:23<3279::AID-ANIE3279>3.0.CO;2-M.

Authors

Masaaki Sakai¹, Masato Ueda¹, Norio Miyaura¹

Affiliation

¹ Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628 (Japan), Fax: (+81) 11-706-6561 or 11-706-7882.

Abstract

Highly inert to ionic additions to aldehydes, aryl- and 1-alkenylboronic acids succumb to a catalytic variant mediated by a [Rh(acac)(CO)₂ ]-diphosphane complex in aqueous phase at 80-95°C to yield secondary alcohols [Eq. (a)]. A key step in the catalytic cycle is the transmetalation between the boron reagent and the rhodium complex. L_n =diphosphane (e.g. 1,1'-bis(diphenylphosphanyl)ferrocene); R=aryl, 1-alkenyl; R'=alkyl, aryl; acac=acetylacetonate.

Keywords: Aldehydes; Boron; Homogeneous catalysis; Nucleophilic additions; Rhodium.