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

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About: Convenient synthesis of non-conjugated alkynyl ketones from keto aldehydes by a chemoselective one-pot nonaflation-base catalyzed elimination sequence Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	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. 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. (en)
Title	Convenient synthesis of non-conjugated alkynyl ketones from keto aldehydes by a chemoselective one-pot nonaflation-base catalyzed elimination sequence Convenient synthesis of non-conjugated alkynyl ketones from keto aldehydes by a chemoselective one-pot nonaflation-base catalyzed elimination sequence (en)
skos:prefLabel	Convenient synthesis of non-conjugated alkynyl ketones from keto aldehydes by a chemoselective one-pot nonaflation-base catalyzed elimination sequence Convenient synthesis of non-conjugated alkynyl ketones from keto aldehydes by a chemoselective one-pot nonaflation-base catalyzed elimination sequence (en)
skos:notation	RIV/61388963:_____/11:00361392!RIV12-AV0-61388963
http://linked.open...avai/predkladatel	Ústav organické chemie a biochemie AV ČR, v. v. i.
http://linked.open...avai/riv/aktivita	Z
http://linked.open...avai/riv/aktivity	Z(AV0Z40550506)
http://linked.open...iv/cisloPeriodika	30
http://linked.open...vai/riv/dodaniDat	2012
http://linked.open...aciTvurceVysledku	Boltukhina, Ekaterina Lyapkalo, Ilya Sheshenev, Andrey
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Ústav organické chemie a biochemie AV ČR, v. v. i.
http://linked.open...dnocenehoVysledku	191953
http://linked.open...ai/riv/idVysledku	RIV/61388963:_____/11:00361392
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	nonaflation; alkynyl ketones; cross-coupling; elimination; phosphazene base (en)
http://linked.open.../riv/klicoveSlovo	alkynyl ketones cross-coupling elimination nonaflation phosphazene base
http://linked.open...odStatuVydavatele	GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV	[EF6894B17403]
http://linked.open...i/riv/nazevZdroje	Tetrahedron
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	3 (xsd:int)
http://linked.open...cetTvurcuVysledku	3 (xsd:int)
http://linked.open...UplatneniVysledku	2011
http://linked.open...v/svazekPeriodika	67
http://linked.open...iv/tvurceVysledku	Boltukhina, Ekaterina Lyapkalo, Ilya Sheshenev, Andrey
http://linked.open...ain/vavai/riv/wos	000292573700003
http://linked.open...n/vavai/riv/zamer	Regulace biologických procesů: Chemické modulátory vybraných systémů významných pro medicínu a zemědělství
issn	0040-4020
number of pages	7 (xsd:int)
http://bibframe.org/vocab/doi	10.1016/j.tet.2011.05.095
is http://linked.open...avai/riv/vysledek of	Convenient synthesis of non-conjugated alkynyl ketones from keto aldehydes by a chemoselective one-pot nonaflation-base catalyzed elimination sequence Convenient synthesis of non-conjugated alkynyl ketones from keto aldehydes by a chemoselective one-pot nonaflation-base catalyzed elimination sequence

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