the heck reaction applied to 1,3- and 1,2-unsaturated derivatives, a way towards molecular complexity到底反应应用于1,3 - 1,2-unsaturated衍生品,对分子的复杂性.pdf

Molecules 2010, 15, 2667-2685; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Review The Heck Reaction Applied to 1,3- and 1,2-Unsaturated Derivatives, a Way towards Molecular Complexity Annamaria Deagostino *, Cristina Prandi, Silvia Tabasso and Paolo Venturello Dipartimento di Chimica Generale e Chimica Organica, Università di Torino, Via Pietro Giuria, 7, I 10125, Torino, Italy * Author to whom correspondence should be addressed; E-Mail: annamaria.deagostino@unito.it; Tel.: +39 0116707074; Fax: +390116707642. Received: 1 February 2010; in revised form: 26 March 2010 / Accepted: 1 April 2010 / Published: 13 April 2010 Abstract: This review is an overview of the last ten years’ use of the Mizoroki–Heck coupling applied to 1,2- and 1,3-dienes. Since both these systems form π-allyl palladium intermediates in Pd(0) coupling, they show particular chemical behavior. Many examples of 1,2-dienes Heck reactions are presented. 1,2-Dienes are important substrates because of their high reactivity that makes them useful building blocks for the synthesis of biologically relevant structures. Keywords: Mizoroki–Heck reaction; palladium; 1,2-dienes; 1,3-dienes 1. Introduction 1,2-Dienes and 1,3-dienes are interesting substrates among the unsaturated systems because of their high reactivity. In fact, when they undergo a carbopalladation process a π-allyl palladium intermediate is formed and at least two reactive pathways have to be considered. If a nucleophile