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Hydrovinylation Reactions – Atom‐Economic Transformations with Steadily Increasing Synthetic Potential
Author(s) -
Hilt Gerhard
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200212
Subject(s) - chemistry , alkene , stereocenter , catalysis , ozonolysis , enantioselective synthesis , atom economy , intermolecular force , styrene , combinatorial chemistry , organic chemistry , molecule , copolymer , polymer
The intermolecular carbon–carbon bond formation between two alkenes also known as 1,2‐hydrovinylation reaction can be realised with different transition metal catalysts. The application of styrene derivatives, norbornenes and other alkenes in asymmetric catalysis with a variety of chiral ligands leads to α‐chiral alkene products in an atom‐economic transformation. Accordingly, the 1,2‐hydrovinylation is one of just a few asymmetric transformations which produce stereogenic centres in the absence of polarised functional groups. The 1,4‐hydrovinylation of terminal alkenes and 1,3‐dienes can be controlled by the electronic nature of the alkene starting material for the selective formation of linear or branched 1,4‐dienes. These adducts can be used for the synthesis of 1,3‐ as well as 1,4‐dicarbonyl derivatives upon ozonolysis of suitable intermediates. As an extension of the 1,4‐hydrovinylation reaction a cobalt‐catalysed 1,4‐hydrobutadienylation reaction is reported where two different 1,3‐dienes react selectively for the formation of 1,3,6‐trienes.