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Convenient synthesis of non-conjugated alkynyl ketones from keto aldehydes by a chemoselective one-pot nonaflation-base catalyzed elimination sequence
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SYSNO ASEP 0361392 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Convenient synthesis of non-conjugated alkynyl ketones from keto aldehydes by a chemoselective one-pot nonaflation-base catalyzed elimination sequence Author(s) Boltukhina, Ekaterina (UOCHB-X)
Sheshenev, Andrey (UOCHB-X)
Lyapkalo, Ilya (UOCHB-X)Number of authors 3 Source Title Tetrahedron. - : Elsevier - ISSN 0040-4020
Roč. 67, č. 30 (2011), s. 5382-5388Number of pages 7 s. Language eng - English Country GB - United Kingdom Keywords nonaflation ; alkynyl ketones ; cross-coupling ; elimination ; phosphazene base Subject RIV CC - Organic Chemistry CEZ AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000292573700003 DOI 10.1016/j.tet.2011.05.095 Annotation Keto aldehydes were selectively converted to non-conjugated alkynyl ketones possessing an unsubstituted alkyne terminus using one-pot nonaflation – base catalyzed elimination reaction sequence. Consecutive one-pot nonaflation of keto aldehydes with perfluorobutane-1-sulfonyl fluoride and elimination of the nonaflyl group using the P1 phosphazene base resulted in the formation of a terminal C-C triple bond with the keto group remaining intact. Careful optimization of the reaction conditions enabled a highly chemoselective conversion of the aldehyde function in the presence of unprotected keto groups exploiting a minor difference in acidity of their alpha-hydrogen atoms. Scope and limitations of the protocol as well as possible implementation of these substrates in Sonogashira coupling were explored. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Year of Publishing 2012
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