85014-12-6Relevant academic research and scientific papers
One-pot, regioselective synthesis of homopropargyl alcohols using pro-pargyl bromide and carbonyl compound by the mg-mediated reaction under solvent-free conditions
Devaramani, Samrat,Li, Shunxi,Ma, Xiaofang,Xu, Daqian,Zhao, Guohu
supporting information, p. 438 - 442 (2020/04/21)
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.
Acyloxy Rearrangement-Triggered Regioselective Hydration of ?-Acetoxy-α,β-Alkynoates/Halo Alkynes
Mendhekar, Kishor L.,Mohapatra, Debendra K.,Pradhan, Tapas R.
, p. 4881 - 4895 (2020/05/01)
Herein, we report a simple, efficient, highly regioselective, and broad-scope hydration method that is facilitated by an unusual interception of an electrophilic intermediate by water generated via acetate group participation during [3,3]-acyloxy rearrang
Re-engineering of PIP3-antagonist triazole PITENIN's chemical scaffold: Development of novel antifungal leads
Pulya, Sravani,Kommagalla, Yadagiri,Sant, Duhita G.,Jorwekar, Shweta U.,Tupe, Santosh G.,Deshpande, Mukund V.,Ramana, Chepuri V.
, p. 11691 - 11701 (2016/02/09)
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
Zinc Amide Catalyzed Regioselective Allenylation and Propargylation of Ketones with Allenyl Boronate
Yamashita, Yasuhiro,Cui, Yi,Xie, Peizhong,Kobayashi, Shu
supporting information, p. 6042 - 6045 (2016/01/09)
Zinc amide catalyzed, regioselective allenylation and propargylation of ketones with allenyl boronate is reported. Tertiary allenyl and homopropargyl alcohols were obtained, respectively, in high selectivities, from the same starting materials, simply by changing the reaction conditions. The substrate scope was wide. Mechanistic studies suggest that the reactions are controlled under kinetic and thermodynamic conditions.
Asymmetric propargylation of ketones using allenylboronates catalyzed by chiral biphenols
Barnett, David S.,Schaus, Scott E.
supporting information; experimental part, p. 4020 - 4023 (2011/10/02)
Chiral biphenols catalyze the enantioselective asymmetric propargylation of ketones using allenylboronates. The reaction uses 10 mol % of 3,3′-Br2-BINOL as the catalyst and allenyldioxoborolane as the nucleophile, in the absence of solvent, and
One-pot, solvent-free regioselective addition reactions of propargyl bromide to carbonyl compounds mediated by Zn-Cu couple
Ma, Xiaofang,Wang, Jin-Xian,Li, Shunxi,Wang, Ke-Hu,Huang, Danfeng
experimental part, p. 8683 - 8689 (2009/12/24)
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.
Highly selective synthesis of acetylenic alcohols promoted by metallic dysprosium in the presence of mercuric chloride
Li, Zhiming,Jia, Yu,Zhou, Jingyao
, p. 2515 - 2524 (2007/10/03)
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.
Carbon-Carbon Bond-Forming Reactions Using Cerium Metal or Organocerium(III) Reagents
Imamoto, Tsuneo,Kusumoto, Tetsuo,Tawarayama, Yoshinori,Sugiura, Yasushi,Mita, Takeshi,et al.
, p. 3904 - 3912 (2007/10/02)
Carbon-carbon bond-forming reactions using cerium metal or organocerium(III) reagents have been investigated.Cerium amalgam is an effective reagent for the chemoselective preparation of homoallylic alcohols from allyl halides and carbonyl compounds.These same reagent can also be satisfactorily employed for the Reformatsky-type reaction of α-halo esters with carbonyl compounds.It has been shown that organocerium(III) reagents are conveniently generated by the reaction of organolithiums with cerium(III)iodide or cerium(III)chloride.The reagents are less basic thanorganolithiums or Grignard reagents, and they react cleanly at -78 to -65 deg C with various carbonyl compounds to afford the addition products in high yields, even though the substrates are susceptible to enolization or metal-halogen exchange with simple organolithiums.The same reagents react also with α,β-unsaturated compounds to yield 1,2-addition products in high selectivity.
