Me2Zn-mediated addition of acetylenes to aldehydes and ketones.
[reaction: see text] Contrary to expectations, commercially available 2 M Me2Zn in toluene is able to promote the addition of phenylacetylene to aldehydes and ketones. This reactivity is determined by a new, unprecedented mechanism, which involves activation of the zinc reagent via coordination with carbonyl substrates that behave "ligand like". Broad scope, high tolerance to functional groups, and a simple procedure make this new method highly interesting for the synthetic chemist.
Dipartimento di Chimica G. Ciamician, Alma Mater Studiorum, Università di Bologna, Via Selmi 2, 40126 Bologna, Italy. piergiorgio.cozzi@unibo.it
Pier Giorgio
PG
Cozzi
Jens
J
Rudolph
Carsten
C
Bolm
Per-Ola
PO
Norrby
Claudia
C
Tomasini