127559-58-4Relevant academic research and scientific papers
Propargylation of aldehydes using potassium allenyltrifluoroborate
Couto, Tlio R.,Freitas, Jucleiton J. R.,Freitas, Juliano C. R.,Cavalcanti, Italo H.,Menezes, Paulo H.,Oliveira, Roberta A.
, p. 71 - 78 (2015)
The commercially available resin Amberlyst A-31 was efficiently used to promote the propargylation of aldehydes using potassium allenyltrifluoroborate. The method is simple and fast, and the products were obtained in short reaction times in high yields and purity at room temperature in a regio- and chemoselective manner.
Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation
Andrade, Silvia R. C. P.,Freitas, Jucleiton J. R.,Freitas, Juliano C. R.,Freitas, Queila P. S. B.,Menezes, Paulo H.,Oliveira, Roberta A.
supporting information, p. 168 - 174 (2020/03/27)
The propargylation of aldehydes promoted by microwave irradiation using allenylboron compounds in a chemo- and regioselective way is described. The corresponding products were obtained in short reaction time, high yield and purity without the need of any solvent when allenylboronic acid pinacol ester was used, or using a minimal amount of acetone when potassium allenyltrifluoroborate was used.
Synthesis, characterization of active Sn(0), and its application in selective propargylation of aldehyde at room temperature in water
Chatterjee, Paresh Nath,Paul, Dipankar,Sawkmie, Micky Lanster,Sinha, Arun Kumar,Khatua, Snehadrinarayan
supporting information, p. 29 - 36 (2019/01/10)
Active Sn(0) particles are synthesized in high yields by the chemical reduction of the blue-black stannous oxide using freshly prepared sodium stannite solution as reducing agent at 40 °C and 60 °C. The Sn(0) particles are characterized using powder XRD, SEM, and DSC. The as-synthesized Sn(0) particles are applied as reagent for the regioselective synthesis of homopropargyl alcohols from propargyl bromide and aldehydes in distilled water at room temperature (in 50%-84% yields). No assistance of heat, microwave, ultrasound, organic co-solvent, co-reagent, or inert atmosphere is required for this reaction. The propargylation reaction is highly chemoselective towards aldehyde over other less electrophilic carbonyl functional groups such as ketone, amide, and carboxylic acid. Our in-house synthesized homopropargyl alcohols can be used to synthesize conjugated 1,3-diynes.
Regioselective propargylation of aldehydes using potassium allenyltrifluoroborate promoted by tonsil
Freitas, Jucleiton J.R.,Couto, Tulio R.,Cavalcanti, Italo H.,Freitas, Juliano C.R.,Barbosa, Queila P.S.,Oliveira, Roberta A.
supporting information, p. 760 - 765 (2016/02/05)
The propargylation of aldehydes using potassium allenyltrifluoroborate promoted by tonsil, an inexpensive and readily available clay, in a chemo- and regioselective way is described. The method is simple and avoids the use of air and moisture sensitive organometallics and products were obtained in good to moderate yields.
Synthesis of allenyl ketones and their palladium-catalyzed cycloisomerization/dimerization: Approaching the limits
Hashmi, A. Stephen K.,Choi, Ji-Hyun,Bats, Jan W.
, p. 342 - 357 (2007/10/03)
The preparation of several new allenyl ketones 1a-j and 1o-q is reported. In the case of allenyl ketones with nucleophilic groups in the side-chain like 1k-m, the material polymerized during the purification procedure; with the dialkyl thioether In the product of a Pummerer isomerization, the acetoxymethyl alkyl thioether, 11 was formed. Depending on the route to 1 sometimes either the acetate adducts 8 and the 1-propynyl ketones 9 or the dipropargyl and propargyl allenyl carbinol 14 and 15 were observed as side-products. Good yields of the sensitive aryl γ-halogen-allenyl ketones 23a and 23b were obtained by a new synthetic route, on the other hand the aryl γ-silylallenyl ketone 23c was readily desilylated. Subjecting the new allenyl ketones to the PdCl2(MeCN)2 catalyst provided the 2-substituted furans 2 and the 2,4-disubstituted furans 3 in most cases. The yields and ratios of these products strongly depended on the nature of the groups being present. With the aryl thioether and the γ-halogen allenyl ketones the palladium-catalyzed reaction failed. Detailed structural information about the new products was provided by the X-ray structure analyses of the p-acetamidophenyl propargyl carbinol 6g and the 2-aryl-4-(1-methyl-3-aryl-3-oxo-propen-1-yl furan 3h. Wiley-VCH Verlag GmbH, 1999.
