Title |
Silica Gel as a Promoter of Sequential Aza‐Michael/Michael Reactions of Amines and Propiolic Esters: Solvent‐ and Metal‐Free Synthesis of Polyfunctionalized Conjugated Dienes
|
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Published in |
Chemistry - An Asian Journal, June 2018
|
DOI | 10.1002/asia.201800645 |
Pubmed ID | |
Authors |
Jovana Aleksić, Milovan Stojanović, Marija Baranac‐Stojanović |
Abstract |
We present an efficient and simple, metal-free and solvent-free silica gel-promoted synthesis of functionalized conjugated dienes by sequential aza-Michael/Michael reactions starting from commercially available primary amines and propiolic esters. The scope and usefulness of the method is demonstrated on 31 examples, including a range of propiolic esters, aliphatic amines and differently substituted aromatic amines. In the case of aliphatic amines, the products are obtanied within 0.5-4 h in 52-85% yield compared with 3.5-22 h under classical solution-phase synthesis, proceeding in similar or lower yields. Particular usefulness of the method is found in the case of weakly nucleophilic aromatic amines, which provide products in 21-73% yield during 2.5-9.5 h compared with 0-49% during 1-6 days under standard solution-phase conditions and in the case of more hydrophobic esters yielding products in 47-79% during 1-3 h compared with 0-45% during 4-114 h in the solvent. |
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