Skeletal Rearrangement Reactions

Skeletal rearrangement reactions, which involve a change of connectivity of the substrate via cleavage of carbon-carbon, carbon-heteroatom, and heteroatom-heteroatom bonds, have attracted much attention as a synthetic method of highly substituted organic molecules. In particular, these transformations often provide poly-substituted aromatic and heteroaromatic compounds in an efficient manner, since aromatization is a principal driving force behind the cleavage of these relatively inert chemical bonds. Catalytic skeletal rearrangement reactions are classified into two processes; (1) reactions via activation through coordination of p-bonds, such as alkynes, allenes, and alkenes, to transition-metal catalysts and (2) reactions via activation through s-coordination of heteroatoms, such as hydroxyl groups.