N-heterocyclic carbene catalyzed additions of 3-trimethylsilyl propiolate to aldehydes

A N-heterocyclic carbene (NHC) catalyzed addition reaction of 3-trimethylsilyl propiolate with aldehydes has been developed. Under the catalysis of 2mol% NHCs, benzaldehyde, furfural, β-naphthaldehyde, meta- and para-substituted aromatic aldehydes reacted with 3-trimethylsilyl propiolate to afford β...

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Published inJournal of Saudi Chemical Society Vol. 20; no. 2; pp. 207 - 212
Main Authors Du, Guang-Fen, Zou, Xiao-Lei, Dai, Bin, He, Lin
Format Journal Article
LanguageEnglish
Published Riyadh, Saudi Arabia Elsevier B.V 01.03.2016
Saudi Chemical Society
Elsevier
Subjects
3-Trimethylsilyl propiolate
Alkynylation
N-heterocyclic carbenes
β-Branched Morita–Baylis–Hillman adducts
Alkynylation
3-Trimethylsilyl propiolate
β-Branched Morita–Baylis–Hillman adducts
N-heterocyclic carbenes
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Summary:A N-heterocyclic carbene (NHC) catalyzed addition reaction of 3-trimethylsilyl propiolate with aldehydes has been developed. Under the catalysis of 2mol% NHCs, benzaldehyde, furfural, β-naphthaldehyde, meta- and para-substituted aromatic aldehydes reacted with 3-trimethylsilyl propiolate to afford β-acylated MBH adducts in good yield with excellent stereoselectivity. While ortho-substituted benzaldehydes coupled with 3-trimethylsilyl propiolate to give alkynylation products as the sole products under the same reaction conditions.
ISSN:1319-6103
DOI:10.1016/j.jscs.2013.12.007