24580-49-2Relevant academic research and scientific papers
Mild conversion of propargylic alcohols to α,β-unsaturated enones in ionic liquids (ILs); A new 'metal free' life for the Rupe rearrangement
Nandi, Ganesh C.,Rathman, Benjamin M.,Laali, Kenneth K.
supporting information, p. 6258 - 6263 (2013/10/22)
A mild and selective transition metal free protocol for the conversion of propargylic alcohols to cyclic and acyclic α,β-unsaturated enones via the Rupe rearrangement is reported. The method utilizes the Br?nsted acidic ionic liquid [BMIM-SO3H][OTf] as catalyst and [BMIM][PF 6] as solvent and offers the potential for recycling and reuse of the IL solvent. The feasibility to synthesize bicyclic fused cyclopentenone derivatives via a Rupe → Aldol → Nazarov sequence utilizing this protocol has also been demonstrated.
Silver-catalyzed direct addition of terminal alkynes to simple cyclic ketones in water
Jia, Zhenhua,Li, Xingshu,Chan, Alberts. C.,Li, Chao-Jun
, p. 2758 - 2762 (2013/02/21)
The first catalytic addition of terminal alkynes to simple cyclic ketones in water catalyzed by silver was developed. Cyclic ketones were reacted with terminal alkynes efficiently in water to give the corresponding propargyl alcohols. Georg Thieme Verlag
Organocatalytic alkynylation of aldehydes and ketones under phase-transfer catalytic conditions
Weil, Torsten,Schreiner, Peter R.
, p. 2213 - 2217 (2007/10/03)
We developed alkynylations of various aldehydes and ketones under practical phase-transfer conditions at room temperature. The straightforward methodology combines one-pot synthesis and simple workup with good to excellent yields for propargylic alcohols derived from aliphatic aldehydes and ketones. Even aromatic aldehydes and ketones, could be transformed to the corresponding propargylic alcohols in somewhat lower yields. The yield depending on the amount of PT catalyst and NaOH concentration was also determined. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).
A new entry in catalytic alkynylation of aldehydes and ketones: Dual activation of soft nucleophiles and hard electrophiles by an indium(III) catalyst
Takita, Ryo,Fukuta, Yuhei,Tsuji, Riichiro,Ohshima, Takashi,Shibasaki, Masakatsu
, p. 1363 - 1366 (2007/10/03)
(Chemical Equation Presented). A new entry in catalytic alkynylation of carbonyl compounds was developed in which dual activation of both soft nucleophiles (terminal alkynes) and hard electrophiles (aldehydes and ketones) is achieved using an indium(III)
Catalytic alkynylation of ketones and aldehydes using quaternary ammonium hydroxide base
Ishikawa, Teruhiko,Mizuta, Tomohiro,Hagiwara, Kumiko,Aikawa, Toshiaki,Kudo, Takayuki,Saito, Seiki
, p. 3702 - 3705 (2007/10/03)
Catalytic alkynylation of diverse ketones and aldehydes using nonmetallic benzyltrimethylammonium hydroxide or a basic resin of the hydroxide type in DMSO is described. Aliphatic or alicyclic carbonyl partners gave satisfactory results, whereas aromatic o
Solvent-free addition of ethynylbenzene to ketones
Miyamoto,Yasaka,Tanaka
, p. 185 - 186 (2007/10/03)
The addition of ethynylbenzene to ketones proceeded efficiently in the absence of a solvent to give tertiary alkynols in good yields.
Cesium hydroxide: A superior base for the catalytic alkynylation of aldehydes and ketones and catalytic alkenylation of nitriles
Tzalis, Dimitrios,Knochel, Paul
, p. 1463 - 1465 (2007/10/03)
The efficient addition of terminal alkynes to aldehydes or ketones to give propargyl alcohols in yields of 66-96% can be achieved by activation with catalytic amounts of CsOH · H2O [Eq.(a)]. A CsOH-catalyzed addition of acetonitrile derivatives
Efficient routes to cyclic 2,3-epoxyalcohols from cycloalkenyl ketones, via cycloalkenyl alcohols
Marson,Walker,Pickering,Harper,Wrigglesworth,Edge
, p. 10317 - 10338 (2007/10/02)
The minimising of torsional strain and non-bonding interactions is proposed as the explanation of high diastereoselectivity observed in the epoxidation of cycloalkenyl alcohols, reported for twenty three examples. The resulting 2,3-epoxyalcohols are key i
