85437-90-7Relevant academic research and scientific papers
A frustrated-Lewis-pair approach to catalytic reduction of alkynes to cis-alkenes
Chernichenko, Konstantin,Madarasz, Adam,Papai, Imre,Nieger, Martin,Leskelae, Markku,Repo, Timo
, p. 718 - 723 (2013/08/23)
Frustrated Lewis pairs are compounds containing both Lewis acidic and Lewis basic moieties, where the formation of an adduct is prevented by steric hindrance. They are therefore highly reactive, and have been shown to be capable of heterolysis of molecular hydrogen, a property that has led to their use in hydrogenation reactions of polarized multiple bonds. Here, we describe a general approach to the hydrogenation of alkynes to cis-alkenes under mild conditions using the unique ansa-aminohydroborane as a catalyst. Our approach combines several reactions as the elementary steps of the catalytic cycle: hydroboration (substrate binding), heterolytic hydrogen splitting (typical frustrated-Lewis-pair reactivity) and facile intramolecular protodeborylation (product release). The mechanism is verified by experimental and computational studies.
STEREO- AND REGIOSPECIFIC SYNTHESES TO PROVIDE CONJUGATED (E, Z)- AND (Z,Z)-ALKANIDES, AND ARYLATED (Z)-ALKENES IN EXCELLENT YIELDS VIA THE PALLADIUM-CATALYZED CROSS COUPLING REACTIONS OF (Z)-1-ALKENYLBORONATES WITH 1-BROMOALKENES AND ARYL IODIDES
Miyaura, Norio,Satoh, Makoto,Suzuki, Akira
, p. 3745 - 3748 (2007/10/02)
Titled alkadienes are obtained in excellent yields stereo- and regiospecifically by cross-coupling between (Z)-1-alkenylboronates and (E)- or (Z)-1-bromoalkenes in the presence of a catalytic amount of Pd(PPh3)4 and sodium ethoxide.
VINYL COPPER REAGENTS-16. SYNTHESIS OF CONJUGATED DIENES VIA THE ADDITION OF VINYL CUPRATES TO ACETYLENE
Alexakis, A.,Normant, J. F.
, p. 5151 - 5154 (2007/10/02)
Some alkenyl cuprates add smoothly to acetylene yielding dienyl cuprates.
