Synthetic chemists cut their teeth on the Grignard reaction, which allows carbon-carbon bonds to be formed. However, the reactive organomagnesium species is seemingly willful—it forms readily only in dry solvents and can revert to its starting material if it reacts first with water. Li and Wang now show that for one particular case, the addition of a phenyl group to an aldehyde, a Grignard-like reaction actually can occur in water and in air. Trimethyl and tributylphenyltin species add to aldehydes to yield the corresponding alcohols in the presence of a rhodium catalyst, which the authors suggest can insert into the bond between the tin atom and the phenyl carbon atom. — PDS
J. Am. Chem. Soc., in press.