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Me2Zn-Mediated Addition of Acetylenes to Aldehydes and Ketones

Pier Giorgio Cozzi,* Jens Rudolph, Carsten Bolm, Per-Ola Norrby and Claudia Tomasini

*Dipartimento di Chimica "G. Ciamician", Alma Mater Studiorum, UniversitÓ di Bologna, Via Selmi 2, 40126 Bologna, Italy, Email: piergiorgio.cozziunibo.it

P. G. Cozzi, J. Rudolph, C. Bolm, P.-O. Norrby, C. Tomasini, J. Org. Chem., 2005, 70, 5733-5736.

DOI: 10.1021/jo050115r (free Supporting Information)


Abstract

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 mechanism, which is discussed. Broad scope, high tolerance to functional groups, and a simple procedure make this new method highly interesting.

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Key Words

propargyl alcohols, alkynylation


ID: J42-Y2005-830