Chemoselectivity of rhodium carbenoids. A comparison of the selectivity for O-H insertion reactions or carbonyl ylide formation versus aliphatic and aromatic C-H insertion and cyclopropanation

Article abstract of DOI:10.1016/S0040-4020(01)81876-7

A range of diazocarbonyl compounds 1-9 containing two different functional groups has been prepared, and their rhodium(II) catalysed decomposition studied as a means of probing the chemoselectivity of carbenoid intermediates. The results indicate that wereas O-H insertion reactions predominate over cyclopropanation and aromatic insertion reactions, carbonyl ylide formation vs other competing processes is more finely balanced, and is catalyst dependent.