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A New Synthesis of Butadienyl- and Styrylboronic Esters: Highly Reactive Intermediates for Suzuki Cross-Coupling

Paolo Balma Tivola, Annamaria Deagostino, Cristina Prandi and Paolo Venturello*

*Dipartimento di Chimica Generale ed Organica Applicata dell'UniversitÓ, Corso Massimo D'Azeglio, 48, I 10125 Torino, Italy, Email: paolo.venturellounito.it

P. B. Tivola, A. Deagostino, C. Prandi, P. Venturello, Org. Lett., 2002, 4, 1275-1277.

DOI: 10.1021/ol0255817


Abstract

A new method for the synthesis of organoborates starting from α,β-unsaturated acetals was developed. The available alkoxy-functionalized butadienyl- and styrylboronic esters cross couple effectively with a broad spectrum of aryl halides under mild conditions. This method provides an effective approach to aromatic ketones.

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Key Words

Suzuki Coupling, Boronates, Aromatic Ketones, Enones


ID: J54-Y2002-600