1743-36-8Relevant academic research and scientific papers
The high stereoselective synthesis of β-alkynyl-enol phosphates
Ding,Huang
, p. 449 - 454 (2001)
A high stereoselective synthesis for β-alkynyl-enol phosphates from β-alkynyl ketone and dialkyl phosphite, via Atherton-Todd reaction, was reported. NaH as base gave a nearly pure Z-isomer.
9-Allenyl-9-BBN: A new reagent for the efficient allenylboration of carbonyl compounds producing the homopropargylic alcohols in high purity and yield
Brown, Herbert C.,Khire, Uday R.,Racherla, Uday S.
, p. 15 - 18 (1993)
A new reagent, 9-allenyl-9-BBN (1), has been developed for the convenient and efficient synthesis of a variety of homopropargylic alcohols.
Gold-Catalyzed Tandem Oxidative Coupling Reaction between β-Ketoallenes and Electron-Rich Arenes to 2-Furylmethylarenes
Yasukawa, Naoki,Yamada, Yutaro,Furugen, Chikara,Miki, Yuya,Sajiki, Hironao,Sawama, Yoshinari
, p. 5891 - 5895 (2021)
A tandem oxidative coupling reaction of β-ketoallenes and arenes was developed, which leads to the formation of 2-furylmethylarenes using AuCl3 and phenyliodine diacetate. The AuIII salt catalyzed the cyclization of β-ketoallenes to form a 2-furylmethyl gold intermediate, and the subsequent C-H functionalization of arenes proceeded smoothly. During the oxidative coupling, nucleophilic additions occurred at the center and terminal carbon atoms of the allene moiety to form C-O and C-C bonds.
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 (2000)
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.
Active metals prepared in liquid ammonia. Zinc and tin-promoted synthesis of β-hydroxyesters, homoallylic and homopropargylic alcohols
Makosza, Mieczyslaw,Grela, Karol,Fabianowski, Wojciech
, p. 9575 - 9580 (1996)
Active zinc and tin provider can be prepared by reduction of ZnCl2 and SnCl2 with sodium in tetrahydrofuran-liquid ammonia mixtures of various compositions. The activity of the reduced zinc depends on concentration of ammonia in the reactors medium Zinc(A) prepared in liquid ammonia (Method A) was much less active then zinc (B) prepared in THF containing 10-20 volume% of liquid ammonia (Method B). The X-ray powder difractiometry data suggested that zinc (H) was less crystalline then zinc (A). The Reformatsky and Barbier type reactions of carbonyl compounds with α-bromoesters, allylic and propargylic bromides in the presence of Zn or Sn prepared by method B gave the corresponding β-hydroxyesters, homollylic and homopropargylic alcohols in good to excellent yields.
Base-promoted direct synthesis of functionalized: N -arylindoles via the cascade reactions of allenic ketones with indoles
Li, Shengxiao,Wu, Xin-Xing,Chen, Shufeng
, p. 789 - 793 (2019)
A convenient Cs2CO3-promoted cascade benzannulation reaction of allenic ketones with indoles was achieved for the synthesis of functionalized N-arylindole derivatives under transition-metal-free conditions. A series of readily available starting materials can undergo the process successfully. It represents a practical method for the construction of N-arylindole scaffolds with high atom economy.
A synthesis of oxolenes and furans via oxacyclopentylidene chromium and molybdenum complexes
Schmidt, Bernd,Kocienski, Philip,Reid, Gillian
, p. 1617 - 1630 (1996)
An easy and convenient preparation of substituted oxolenes and furans by metal-assisted cyclization of alkynols using labile pentacarbonylchromium and pentacarbonylmolybdenum complexes is described.
A new method for the preparation of 1,3-dilithiopropyne: An efficient synthesis of homopropargyl alcohols
Cabezas, Jorge A,Pereira, Albán R,Amey, Adam
, p. 6819 - 6822 (2001)
Controlled dilithiation of propargyl bromide with two equivalents of n-butyllithium, in the presence of TMEDA, produces the operational equivalent of the dianion 1,3-dilithiopropyne. The latter reacts efficiently with aldehydes and ketones to produce homo
Organoboranes for Synthesis. 15. B-Allenyl-9-BBN: A Highly Regiospecific and Chemoselective Reagent for Allenylboration of Representative Carbonyl Compounds, Leading to Homopropargylic Alcohols and Amines
Brown, Herbert C.,Khire, Uday R.,Narla, Gowriswari,Racherla, Uday S.
, p. 544 - 549 (1995)
Reactions of B-allenyl-9-BBN (11) with representative carbonyl compounds, such as aldehydes, ketones, acid chlorides, carboxylic acid esters, and imines, proceed cleanly with the allenyl moiety undergoing transfer to the carbonyl or imine carbon, with allenic to propargylic rearrangement, and the boron moiety to the carbonyl oxygen or imine nitrogen.A simple oxidation with alkaline hydrogen peroxide results in the formation of the corresponding homopropargylic alcohols and amines in excellent yields.Aldehydes, ketones, and imines react in a 1:1 stoichiometry, while acid chlorides and carboxylic acid esters react with 2 equiv of the reagent.The relative reactivities of representative aldehydes, ketones, and esters toward 11 were also explored.Besides being highly regiospecific, the reagent 11 also possesses a remarkable chemoselectivity.B-Allenyl-9-BBN can distinguish between less and more sterically hindered aldehydes, ketones, and esters, making possible the clean and selective propargylboration of a desired carbonyl group in complex organic molecules containing less reactive functional groups.
Regioselective one-pot synthesis of 1,4-disubstituted 1,2,3-triazole derivatives
Gümü, Ayegül,Uur, Sibel
, p. 361 - 364 (2014)
The one-pot synthesis of novel 1,4-disubstituted 1,2,3-triazole derivatives derived from homopropargyl alcohol backbones has been accomplished. Triazoles are obtained in good yields from a variety of readily available aromatic and aliphatic halides withou
