Me2Zn-mediated addition of acetylenes to aldehydes and ketones

被引:52
作者
Cozzi, PG
Rudolph, J
Bolm, C
Norrby, PO
Tomasini, C
机构
[1] Univ Bologna, Dipartimento Chim G Ciamician, Alma Mater Studiorum, I-40126 Bologna, Italy
[2] Univ Aachen, Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
[3] Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark
关键词
D O I
10.1021/jo050115r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:5733 / 5736
页数:4
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