One-pot, regioselective synthesis of homopropargyl alcohols using pro-pargyl bromide and carbonyl compound by the mg-mediated reaction under solvent-free conditions
The elimination of volatile organic solvents in organic synthesis is the most important goal in “Green” chemistry. We report a simple, efficient and facile method for the addition of progargyl bromide to carbonyl compounds using Mg metal as a mediator under solvent-free conditions which could regioselectively generate homopropargyl alcohols efficiently in good to excellent yields. The procedure has advantages such as short reaction time, operationally simple, excellent product yields, high regioselectivity and organic solvent-free.
Re-engineering of PIP3-antagonist triazole PITENIN's chemical scaffold: Development of novel antifungal leads
A novel 4-(1-phenyl-1-hydroxyethyl)-1-(o-hydroxyphenyl)-1H-1,2,3-triazole was designed by integrating the structural features of triazole PITENIN anticancer agents and the azole class of antifungal drugs. A two-step protocol comprising the Barbier proparg
Copper-catalyst-controlled site-selective allenylation of ketones and aldehydes with propargyl boronates
A practical and highly site-selective copper-PhBPE-catalyst-controlled allenylation with propargyl boronates has been developed. The methodology has shown to be tolerant of diverse ketones and aldehydes providing the allenyl adducts in high selectivity. T
Fandrick, Keith R.,Ogikubo, Junichi,Fandrick, Daniel R.,Patel, Nitinchandra D.,Saha, Jaideep,Lee, Heewon,Ma, Shengli,Grinberg, Nelu,Busacca, Carl A.,Senanayake, Chris H.
supporting information
p. 1214 - 1217
(2013/05/09)
One-pot, solvent-free allylation or propargylation of carbonyl compounds mediated by the in situ generated Zn-Ag couple
Zn-Ag couple which was in situ generated by zinc being oxidized with catalytic silver acetate was successfully applied to the one-pot and solvent-free allylation or propargylation of carbonyl compounds, in which high yields, regioselective addition, waste minimization and simple operation can be achieved.
Yu, Changquan,Yang, Jian,Xia, Lingjie,Lu, Xiuyang
experimental part
p. 2484 - 2486
(2012/08/27)
Zinc catalyzed and mediated propargylations with propargyl boronates
Chemical Equation Presented The utility of allenyl and propargyl boronates for the propargylation of aldehydes and ketones mediated by zinc is presented. The reaction is catalytic in zinc with allenyl or propargyl borolanes. The propargylation with crystalline and air-stable propargyl diethanolamine boronates was also achieved. A catalytic cycle is proposed, and preliminary mechanistic studies are discussed.
Fandrick, Daniel R.,Fandrick, Keith R.,Reeves, Jonathan T.,Tan, Zhulin,Johnson, Courtney S.,Lee, Heewon,Song, Jinhua J.,Yee, Nathan K.,Senanayake, Chris H.
supporting information; experimental part
p. 88 - 91
(2010/03/03)
One-pot, solvent-free regioselective addition reactions of propargyl bromide to carbonyl compounds mediated by Zn-Cu couple
A Barbier-type propargylation of carbonyl compounds with propargyl bromide has been achieved with reactive zinc-copper couple under solvent-free conditions. The reaction of aldehydes with propargyl bromide produced the unique homopropargyl alcohols in excellent yields at room temperature without the formation of homoallenyl alcohols. The ketones reacted with propargyl bromide to give the corresponding homopropargyl alcohols in good to excellent yields at -14 to -16 °C. The advantages of this method are excellent yields, short reaction time, high regioselectivity, and avoidance of the use of organic solvents.
Synthesis of homopropargyl alcohols via sonochemical Barbier-type reaction
A series of homopropargyl alcohols were synthesized from the reaction mixture of zinc powder, 1,2-diiodoethane, 3-bromo-1-propyne and aldehyde or ketone in anhydrous THF under ultrasound. The homopropargyl alcohols were obtained as the only product in all cases when aldehydes were reacted with 3-bromo-1-propyne under this sonochemical Barbier-type reaction condition. The homopropargyl alcohol was produced as the major product and the low contamination of allenyl alcohol was also obtained when ketone was used as substrate under the reaction condition.
Lee, Adam Shih-Yuan,Chu, Shu-Fang,Chang, Yu-Ting,Wang, Shu-Huei
p. 1551 - 1553
(2007/10/03)
Highly selective synthesis of acetylenic alcohols promoted by metallic dysprosium in the presence of mercuric chloride
Promoted by metallic dysprosium, carbonyl compounds react smoothly with propargyl bromide to afford the corresponding homopropargylic alcohols in good to excellent yields without observation of allenic alcohols. In addition, this reaction is regioselective and chemoselective.
Li, Zhiming,Jia, Yu,Zhou, Jingyao
p. 2515 - 2524
(2007/10/03)
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