17684-06-9Relevant academic research and scientific papers
Palladium-catalyzed regio- and stereoselective cross-addition of terminal alkynes to ynol ethers and synthesis of 1,4-enyn-3-ones
Haribabu, Madala,Dwivedi, Vikas,Kant, Ruchir,Sridharreddy, Maddi
, p. 3783 - 3786 (2015/03/18)
Conjugated enynes, enol ethers, and enynones are versatile building blocks that can be elaborated by a wide variety of synthetic transformations. The selective synthesis of such units is a prerequisite for their effective utilization. The synthesis of conjugated 2-phenoxyenynes through a palladium-catalyzed cross-addition of terminal alkynes to phenylethynyl ethers (hydroalkynylation) is now presented. The reaction is highly regio-, stereo-, and chemoselective, and shows excellent tolerance toward functional groups. The addition further features very mild reaction conditions (room temperature) and an inexpensive catalytic system (without a ligand and with a cheaply available Pd catalyst). The thus synthesized enynyl ethers with allylic hydroxy tethers, which survived the reaction, were shown to be ready precursors for valuable 1-en-4-yn-3-ones. Alkyne plus alkyne: The hydroalkynylation of phenoxy alkynes was achieved with high regio-, chemo-, and stereoselectivities. A catalytic amount of [Pd(PPh3)2Cl2] with 2.5equiv. of NEt3 could mediate the reaction without the need for a ligand, or a Cu catalyst for the activation of the terminal alkyne. The products with allylic hydroxy tether are convenient precursors for useful enynones. pTSA=p-toluenesulfonic acid.
Palladium-catalyzed acylation and/or homo-coupling of aryl- and alkyl-acetylenes
Perrone, Serena,Bona, Fabio,Troisi, Luigino
experimental part, p. 7386 - 7391 (2011/10/09)
Allyl or benzyl halides, through a Pd(0)-catalyzed reaction and under CO pressure, generate acyl-palladium/halides that, in the presence of a base and an aryl- and alkyl-acetylene, undergo nucleophilic acyl substitution giving conjugated acetylenic ketones. Diynes, resulting from alkyne/alkyne homo-coupling, were instead the main products in reactions performed without allyl or benzyl halides. Moreover, dimerization, trimerization, and cyclotrimerization reactions of acetylenes were observed in reaction carried out even without base.
Atom-efficient metal-catalyzed cross-coupling reaction of indium organometallics with organic electrophiles
Perez,Sestelo,Sarandeses
, p. 4155 - 4160 (2007/10/03)
The novel metal-catalyzed cross-coupling reaction of indium organometallics with organic electrophiles is described. Triorganoindium compounds (R3In) containing alkyl, vinyl, aryl, and alkynyl groups are efficiently prepared from the correspond
