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Journal Article Synthesis of β-ketonitriles, α,β-alkynones and biscabinols from esters using tert-butoxide-assisted C(O)–C (i.e., acyl–C) coupling under ambient conditions
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Authors
Bo Ram Kim, Hyung-Geun Lee, Seung-Beom Kang, Kwang-Ju Jung, Gi Hyeon Sung, Jeum-Jong Kim, Sang-Gyeong Lee, Yong-Jin Yoon
Issue Date
2013-12
Citation
Tetrahedron, v.69, no.48, pp.10331-10336
ISSN
0040-4020
Publisher
Elsevier
Language
English
Type
Journal Article
DOI
https://dx.doi.org/10.1016/j.tet.2013.10.007
Abstract
We demonstrated the synthesis of 棺-ketonitriles, 慣,棺- alkynones, and biscarbinols using tert-butoxide-assisted C(CO)-C (i.e., acyl-C) coupling of esters under ambient conditions. tert-Butoxide-assisted C(CO)-C (i.e., acyl-C) coupling of esters with cyanomethylenes and acetylenes under transition metal-free ambient conditions gives 棺-ketonitriles, 慣,棺-alkynones and/or aryl bis(phenylethynyl)carbinols in moderate-to-good yields. It is noteworthy that this is a rapid, facile, and efficient process under ambient conditions, and use of cheap and stable starting materials. © 2013 Elsevier Ltd. All rights reserved.
KSP Keywords
Metal-free, Transition metal, ambient conditions, tert-butoxide(Niobium penta)