New studies of Rh-catalyzed addition of boronic acids under basic conditions in aqueous medium

• Published in: Tetrahedron letters Vol. 43; no. 34; pp. 5905 - 5908
• Main Authors: Amengual, Rémi, Michelet, Véronique, Genêt, Jean-Pierre
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 19.08.2002; Elsevier
• Subjects: boronic acids; Chemistry; Chemistry, Organic; Physical Sciences; recyclable rhodium/ m-TPPTC system; Science & Technology; styrene derivatives; water-soluble ligand; α,β-unsaturated ketones; water-soluble ligand; recyclable rhodium/ m-TPPTC system; styrene derivatives; α,β-unsaturated ketones; boronic acids; ROUTE; alpha,beta-unsaturated ketones; OLEFINS; EFFICIENT; DERIVATIVES; ARYLBORONIC ACIDS; recyclable rhodium/m-TPPTC system; CONJUGATE ADDITION; WATER
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/S0040-4039(02)01274-1

Rh-catalyzed CC bond formation in neat water under basic conditions has been efficiently performed. The addition of various boronic acids to styrene, 2-vinylpyridine, and cyclic α,β-unsaturated ketones has been realized with high selectivity and yield. We have shown that m-TPPTC (tris( m-carboxyphenyl)phosphane trilithium salt) exhibited a higher reactivity compared to TPPTS. These couplings could also be conducted very efficiently under basic and phosphaneless conditions to give functionalized aryl derivatives. The benefits of the additional anionic ligand m-TPPTC lied in the successful recycling experiments of 1,4-addition of phenylboronic acid to cyclohexenone, with no loss of the water-soluble catalyst. Graphic