Ring-closing metathesis as a basis for the construction of aromatic compounds.
The use of metathesis, especially in the context of ring-closing metathesis (RCM) to form five- and six-membered rings, is widespread in organic chemistry today. However, there are surprisingly few examples of the reaction being used to form aromatic compounds. The central place of aromatic compounds in both medicinal chemistry and natural products synthesis, coupled with the efficiency and functional group tolerance of RCM catalysts, means that there is now an interesting opportunity to use RCM for the synthesis of arenes. Although the formation of an aromatic compound was viewed in many early examples as an undesirable degradation product, several rationally designed methods towards the preparation of aromatic compounds by RCM have recently been developed.
Donohoe
Timothy J
TJ
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK. timothy.donohoe@chem.ox.ac.uk
Orr
Allan J
AJ
Bingham
Matilda
M
D003500:Cyclization; D007536:Isomerism; D008956:Models, Chemical; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000737:chemistry
D011758:Pyrroles