Me2Zn-mediated addition of acetylenes to aldehydes and ketones.

J Org Chem

Dipartimento di Chimica G. Ciamician, Alma Mater Studiorum, Università di Bologna, Via Selmi 2, 40126 Bologna, Italy.

Published: July 2005

[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.

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http://dx.doi.org/10.1021/jo050115rDOI Listing

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