Počet záznamů: 1

Convenient synthesis of non-conjugated alkynyl ketones from keto aldehydes by a chemoselective one-pot nonaflation-base catalyzed elimination sequence

  1. 1.
    0361392 - UOCHB-X 2012 RIV GB eng J - Článek v odborném periodiku
    Boltukhina, Ekaterina - Sheshenev, Andrey - Lyapkalo, Ilya
    Convenient synthesis of non-conjugated alkynyl ketones from keto aldehydes by a chemoselective one-pot nonaflation-base catalyzed elimination sequence.
    Tetrahedron. Roč. 67, č. 30 (2011), s. 5382-5388 ISSN 0040-4020
    Výzkumný záměr: CEZ:AV0Z40550506
    Klíčová slova: nonaflation * alkynyl ketones * cross-coupling * elimination * phosphazene base
    Kód oboru RIV: CC - Organická chemie
    Impakt faktor: 3.025, rok: 2011

    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.
    Trvalý link: http://hdl.handle.net/11104/0198714