93321-44-9Relevant articles and documents
Indium tribromide-catalyzed deacetoxylation of propargylic acetate with triethylsilane
Sakai, Norio,Hirasawa, Maki,Konakahara, Takeo
, p. 6407 - 6409 (2005)
Indium(III) bromide catalyzed the deacetoxylation of propargylic acetates with Et3SiH to produce the corresponding internal alkynes containing a variety of functional groups in good yields.
Catalytic Electrophilic Thiocarbocyclization of Allenes
Jiang, Quanbin,Li, Huimin,Zhao, Xiaodan
supporting information, p. 8777 - 8782 (2021/11/17)
An efficient approach via catalytic electrophilic thiocarbocyclization of allenes to construct indene-based sulfides with excellent regioselectivities is disclosed. The reactions were carried out at low temperatures by selenide catalysis in the presence o
Harnessing Nucleophilicity of Allenol Ester with p-Quinone Methides via Gold Catalysis: Application to the Synthesis of Diarylmethine-Substituted Enones
Sharma, Brijesh M.,Rathod, Jayant,Gonnade, Rajesh G.,Kumar, Pradeep
, p. 9353 - 9363 (2018/06/29)
A gold(I)-catalyzed protocol for intermolecular 1,6-conjugate addition of nucleophilic allenol ester generated in situ through [3,3]-sigmatropic rearrangement with p-quinone methides (p-QMs) has been developed. The gold catalyst plays a dual role by the acid-triggered activation of alkynes and at the same time as a Lewis acid for activation of p-QMs toward nucleophilic attack. This method enables rapid access to a wide range of densely functionalized diarylmethine-substituted enones, a Morita-Baylis-Hillman (MBH) product with high selectivity, excellent yields, and broad substrate scope.
Palladium-catalyzed, ligand-free SN2’ substitution reactions of organoaluminum with propargyl acetates for the synthesis of multi-substituted allenes
Shao, Xuebei,Wen, Chang,Zhang, Gang,Cao, Kangping,Wu, Ling,Li, Qinghan
, p. 68 - 75 (2018/06/29)
We describe a convenient method for the synthesis of multi-substituted allenes from SN2′ substitution reactions organoaluminum with propargyl acetates: The SN2′ substitution reaction of organoaluminum (0.4 mmol) with propargyl acetat
Synthesis of multi-substituted allenes from organoalane reagents and propargyl esters by using a nickel catalyst
Shao, Xue Bei,Zhang, Zhen,Li, Qing Han,Zhao, Zhi Gang
, p. 4797 - 4806 (2018/07/13)
A highly efficient and simple route for the synthesis of multi-substituted allenes has been developed by a nickel catalyzed SN2′ substitution reaction of propargyl esters with organic aluminium reagents under mild conditions, which gave the corresponding multi-substituted allenes in good to excellent yields (up to 92%) and high selectivities (up to 99%) at 60 °C for 6 h in THF. Aryls bearing electron-donating or electron-withdrawing groups in propargyl esters gave products in good yields. In addition, the multi-substituted allenes bearing a thienyl or a pyridyl group were obtained in 95-97% selectivities with isolated yields of 72-83%. Furthermore, the SN2′ substitution reaction worked efficiently with propargyl carbonate compounds as well. On the basis of the experimental results, a possible catalytic cycle has been proposed.
Highly Efficient Synthesis of Multi-Substituted Allenes from Propargyl Acetates and Organoaluminum Reagents Mediated by Palladium
Zhang, Zhen,Shao, Xuebei,Zhang, Gang,Li, Qinghan,Li, Xinying
, p. 3643 - 3653 (2017/08/16)
A simple and mild catalytic S N 2′ substitution reaction of propargyl acetates with organoaluminum reagents is reported. The S N 2′ substitution reaction of propargyl acetates with organoaluminum reagents mediated by Pd(PhP 3) 2 Cl 2 (1 mol%)/PPh 3 (2 mol%)/K 2 CO 3 in tetrahydrofuran at 60 °C for 3-4 hours afforded the corresponding multi-substituted allenes in good yields (up to 94%) with high selectivities (up to 99%). The process was simple and easily performed, which offers an efficient method to synthesize the multi-substituted allene derivatives.
Synthesis of Multisubstituted Allenes via Palladium-Catalyzed Cross-Coupling Reaction of Propargyl Acetates with an Organoaluminum Reagent
Zhang, Zhen,Mo, Song,Zhang, Gang,Shao, Xuebei,Li, Qinghan,Zhong, Ying
, p. 611 - 614 (2017/03/11)
We describe a convenient method for the synthesis of multisubstituted allenes from cross-coupling of propargyl acetates with -organoaluminum reagent: The reaction of propargyl acetates with 1.2 equivalents of organoaluminum reagent mediated by Pd(PPh3)2Cl2 (1 mol%)/Ph3P (2 mol%) and K2CO3 in THF may produce tri- or tetrasubstituted allenes in good to excellent yields (83-94%) and high regio-selectivities (up to 99%) at 60 °C in 3-4 hours.
Co2(CO)8-mediated Selective Reductions of Propargyl Alcohol Derivatives to Alkenes
Dou, Ying,Xing, Ping,Huang, Zuogang,Jiang, Biao
supporting information, p. 999 - 1002 (2016/02/18)
In the presence of Co2(CO)8 and additives, propargyl alcohol derivatives could be reduced to alkenes in moderate to good yield. The selectivity of this reaction could be controlled by adding different additives: with H2O as the additive, the major configuration of product is Z-alkene; with CF3COOH as the additive, the major configuration of product is E-alkene.
Titanocene-catalyzed metallation of propargylic acetates in homopropargyl alcohol synthesis
Meloche, Jennifer L.,Vednor, Peter T.,Gianino, Joseph B.,Oliver, Allen G.,Ashfeld, Brandon L.
supporting information, p. 5025 - 5028 (2015/01/09)
The titanium-catalyzed metallation and subsequent carbonyl addition of propargylic acetates enable the direct formation of homopropargylic alcohols in good yields. The corresponding products were obtained as single regioisomers without the corresponding a
Highly efficient synthesis of allenes from trimethylaluminum reagent and propargyl acetates mediated by a palladium catalyst
Li, Qing-Han,Jeng, Jung-Yuan,Gau, Han-Mou
, p. 7916 - 7923 (2015/02/02)
A series of propargyl acetates were prepared and used as propargyl electrophiles for coupling reactions with trimethylaluminum. The simple catalytic system of palladium(II) acetate (1 mol-%) and tri(o-tolyl)phosphine (2 mol-%) worked efficiently for a wide variety of aromatic and aliphatic propargyl acetates, producing the substituted allenes in good to excellent yields of up to 94% in tetrahydrofuran. The process was simple and easily performed, and it provides an efficient method for the synthesis of substituted allene derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.
