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.
Highlights
This review is an overview of the last ten years’ use of the Mizoroki–Heck coupling applied to 1,2- and 1,3-dienes
As described in Scheme 1, allenes undergo carbopalladation and for this reason have been widely exploited in organic synthesis as useful intermediates for biologically relevant compounds
The aromatic group attacks the central sp carbon of the allenic moiety creating the corresponding π-allyl palladium intermediate 1, and the nucleophile attacks the less hindered
Summary
1,2-Dienes and 1,3-dienes are interesting substrates among the unsaturated systems because of their high reactivity When they undergo a carbopalladation process a π-allyl palladium intermediate is formed and at least two reactive pathways have to be considered. As described in Scheme 1, allenes undergo carbopalladation and for this reason have been widely exploited in organic synthesis as useful intermediates for biologically relevant compounds In this case, the aromatic group attacks the central sp carbon of the allenic moiety creating the corresponding π-allyl palladium intermediate 1, and the nucleophile attacks the less hindered. When conjugated dienes are involved in the Pd(0) coupling, both the 1,4- and 1,2-addition products (5 and 6 in Scheme 1) are produced as a consequence of the nucleophile entry, whereas the corresponding substituted 1,3-diene 7 is obtained as the result of an elimination process.
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