685881-19-0Relevant articles and documents
A general and efficient FeCl3-catalyzed nucleophilic substitution of propargylic alcohols
Zhan, Zhuang-Ping,Yu, Jing-Liang,Liu, Hui-Juan,Cui, Yuan-Yuan,Yang, Rui-Feng,Yang, Wen-Zhen,Li, Jun-Ping
, p. 8298 - 8301 (2006)
A general and efficient FeCl3-catalyzed substitution reaction of propargylic alcohols with carbon- and heteroatom-centered nucleophiles such as allyl trimethylsilane, alcohols, aromatic compounds, thiols, and amides, leading to the construction of C-C, C-O, C-S and C-N bonds, has been developed.
Amberlite IR-120H as an efficient and versatile solid phase catalyst for nucleophilic substitution of propargylic alcohols
Gujarathi, Satheesh,Hendrickson, Howard P.,Zheng, Guangrong
, p. 3550 - 3553 (2013/07/05)
A highly efficient Amberlite IR-120H resin mediated nucleophilic substitution of the hydroxyl group of propargylic alcohols with a wide range of nucleophiles is reported. The reactions were achieved under very mild conditions in excellent yields.
Iron-catalyzed direct synthesis of densely Substituted benzofurans and naphthopyrans from phenolic compounds and propargylic alcohols
Yuan, Feng-Quan,Han, Fu-She
supporting information, p. 537 - 547 (2013/05/08)
A one-pot cascade reaction for the synthesis of polysubstituted benzofurans and naphthopyrans from simple phenols and propargylic alcohols catalyzed by iron(III) is presented. The results demonstrate that the structural specificity for the formation of fu
Electrophilic chemistry of propargylic alcohols in imidazolium ionic liquids: Propargylation of arenes and synthesis of propargylic ethers catalyzed by metallic triflates [Bi(OTf)3, Sc(OTf)3, Yb(OTf) 3], TfOH, or B(C6F5)3
Aridoss, Gopalakrishnan,Sarca, Viorel D.,Ponder Jr, James F.,Crowe, Jessica,Laali, Kenneth K.
experimental part, p. 2518 - 2529 (2011/05/13)
Metallic triflates M(OTf)3 (M = Bi, Sc, Yb), immobilized in imidazolium ionic liquids [BMIM][BF4], [BMIM][PF6] and [BMIM][OTf] are efficient systems for one-pot reactions of propargylic alcohols 1,3-diphenyl-2-propyn-1-ol Ia, 1-methyl-3-phenyl-2-propyn-1-ol Ib, and 2-pentyn-1-ol Ic, with a wide range of arenes bearing activating substituents, under mild conditions. The [BMIM][PF6]/B(C6F 5)3 and [BMIM][PF6]/TfOH systems were superior in propargylation with Ib and Ic, while reaction of 3-phenyl-2-propyn-1-ol Id with activated aromatics resulted in the formation of diaryl-propanones instead. Propargylation of anisole with Ib under M(OTf)3 catalysis is highly para selective, but with TfOH or B(C6F5)3 as catalyst the ortho isomer was also formed. Steric influence of the propargylic moiety on substrate selectivity is reflected in the lack of ortho propargylation for phenol and ethylbenzene by using propargylic alcohol Ia, and notable formation of the ortho isomer employing alcohol Ib. In the later case para selectivity could be increased by running the reaction at r. t. for 10 h. The Bi(OTf)3-catalyzed reaction of 1,3-dimethoxybenzene with Ia led to minor formation of dipropargylated derivative, along with the monopropargyl product. Propargylation of the less reactive arenes (mesitylene, ethylbenzene, toluene), using Sc(OTf)3 as catalyst, led increasingly to the formation of dipropargylic ethers and propargyl ketones, with no ring propargylation product with toluene. Concomitant formation of dipropargylic ether was also observed in Yb(OTf)3-catalyzed propargylation of β-naphthol, whereas propargylation of 2-nitro and 4-nitro-aniline led to N-propargylation. The recycling/reuse of the IL was demonstrated in representative cases with no appreciable decrease in the conversions over 3 cycles. It was also shown that recycled IL could be used to propargylate a different aromatic compound. The efficacy of IL/M(OTf)3 and IL/TfOH systems for cross-breeding two propargylic alcohols or a propargylic alcohol with a non-propargylic alcohol and/or self-coupling, to form a wide variety of functionalized ethers is also demonstrated.
Iron-catalyzed regioselective hydroaryloxylation of C≡C Triple Bonds: An efficient synthesis of 2H-1-benzopyran derivatives
Xu, Xiaobing,Liu, Jun,Liang, Linfeng,Li, Hongfeng,Li, Yanzhong
supporting information; experimental part, p. 2599 - 2604 (2009/12/31)
An efficient, regioselective, iron-catalyzed intramolecular hydroaryloxylation of 2-propargylphenols or naphthols is reported. The reactions proceed through an endo-dig cyclization to afford benzopyran or naphthopyran derivatives in good to high yields us
PMA-silica gel catalyzed propargylation of aromatic compounds with arylpropargyl alcohols under solvent-free conditions
Srihari, Pabbaraja,Reddy, Joolakanti Shyam Sunder,Mandal, Satadru Sekhar,Satyanarayana, Kamani,Yadav, Jhillu Singh
experimental part, p. 1853 - 1860 (2009/04/04)
PMA-silica gel has been utilized to catalyze efficiently the propargylation of aromatic compounds with arylpropargyl alcohols in the absence of solvent under environmentally benign conditions.
BiCl3-catalyzed propargylic substitution reaction of propargylic alcohols with C-, O-, S- and N-centered nucleophiles
Zhan, Zhuang-Ping,Yang, Wen-Zhen,Yang, Rui-Feng,Yu, Jing-Liang,Li, Jun-Ping,Liu, Hui-Juan
, p. 3352 - 3354 (2008/09/19)
A general and efficient BiCl3-catalyzed substitution reaction of propargylic alcohols with carbon and heteroatom-centered nucleophiles such as allyl trimethylsilane, alcohols, aromatic compounds, thiols and amides, leading to the construction o
Rhenium-catalyzed aromatic propargylation
Kennedy-Smith, Joshua J.,Young, Lauren A.,Toste, F. Dean
, p. 1325 - 1327 (2007/10/03)
A mild aromatic propargylation reaction, employing an air- and moisture-tolerant rhenium-oxo complex ((dppm)ReOCl3) as a catalyst and a propargyl alcohol as the electrophile, is described. The reaction tolerates a broad range of functional groups and regioselectively affords propargylic arenas without formation of the isomeric allenyl adducts. The potential of this rhenium(V)-catalyzed reaction is exemplified by application of the propargylation to the synthesis of O-methyldetrol, mimosifoliol, and β-apopicropodophyllin.
