120615-75-0

Upstream product

• 720-44-5 1-(4-methoxyphenyl)-1-phenylmethanol 
• 536-74-3 phenylacetylene 
• 62698-35-5 1-phenyl-1-p-methoxyphenyl-3-phenylpropargyl alcohol 
• 93321-44-9 1,3-diphenylprop-2-yn-1-yl acetate 
• 5720-07-0 4-methoxyphenylboronic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 100-52-7 benzaldehyde 
• 100-66-3 methoxybenzene 
• 1817-49-8 1,3-diphenyl-1-propyn-3-ol 

Relevant academic research and scientific papers

FeCl3-catalyzed propargylation of aromatic compounds with propargylic acetates

A new method for the synthesis of propargylated aromatic compounds is developed. The reaction was carried out at room temperature in the presence of a catalytic amount of FeCl3 in acetonitrile, high product yields were obtained with excellent r

SeCl2-Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes

A novel and efficient SeCl2-mediated chalcogenative cyclization strategy toward 3-selenophen-3-yl-1H-indoles from readily available and conveniently substituted propargyl indoles is described. It entails an unprecedented selenirenium-induced 1,

Transition-Metal-Catalyst-Free Cross-Coupling Reaction of Secondary Propargylic Acetates with Alkenyl- and Arylboronic Acids

A cross-coupling reaction between secondary propargylic acetates and alkenylboronic acids proceeded to give 1,4-enynes in good yields without addition of transition metal catalyst and base. This simple protocol was also applicable to arylboronic acids, which gave 3-arylated alkynes in good yields. The observed induction period suggested that the reaction of propargylic acetates and organoboronic acids was affected by the in-situ generated AcOH as a catalyst, which was confirmed by a separate experiment.

How Understanding the Role of an Additive Can Lead to an Improved Synthetic Protocol without an Additive: Organocatalytic Synthesis of Chiral Diarylmethyl Alkynes

The use of additives for organic synthesis has become a common tactic to improve the outcome of organic reactions. Herein, by using an organocatalytic process for the synthesis of chiral diarylmethyl alkynes as a platform, we describe how an additive is involved in the improvement of the process. The evolution of an excellent synthetic protocol has been achieved in three stages, from 1) initially no catalyst turnover, to 2) good conversion and enantioselectivity with a superior additive, and eventually 3) even better efficiency and selectivity without an additive. This study is an important and rare demonstration that understanding the role of additive can be so beneficial as to obviate the need for the additive.

Br?nsted Acid-Catalyzed Reactions of Trifluoroborate Salts with Benzhydryl Alcohols

Br?nsted acid-catalyzed carbon-carbon bond forming methodology using potassium alkynyl- and alkenyltrifluoroborate salts has been developed. Organotrifluoroborates react with benzhydryl alcohols to afford a broad range of alkynes and alkenes in good to excellent yields. This protocol features good atom economy because organotrifluoroborate salts and alcohols react in a 1:1 ratio. Furthermore, a variety of unprotected functional groups were tolerated under the developed conditions, including amide, aldehyde, free hydroxyl, and carboxylic acid.

Bronsted acid ionic liquid as a solvent-conserving catalyst for organic reactions

A sulfonyl-containing ammonium-based Bronsted acid ionic liquid was prepared and used as a liquid heterogeneous catalyst for organic reactions. The unique macroscopic phase heterogeneity of the IL in the reaction system not only ensures an excellent catalytic activity of the IL catalyst but also avoids the use of organic reaction solvents. The catalyst system is applicable for a wide range of reactions.

Indium(III) catalyzed direct sp3-sp C-C bond formation from alcohols and terminal alkynes

A simple and efficient indium(III)-catalyzed sp3-sp C-C bond formation reaction via direct coupling of alcohols with terminal alkynes has been developed under mild conditions without any ligand, base or additive, in which both of aromatic and aliphatic alkynes and various alcohols such as benzylic, allylic and propargylic alcohols can be tolerated. This simple reaction system provides an attractive approach to a large number of internal alkynes in moderate to good yields, and only generates H2O as the side product.

SnCl2-catalyzed propargylic substitution of propargylic alcohols with carbon and nitrogen nucleophiles

A weak Lewis acid, tin(II) chloride, which is insensitive to water and air, functioned as a catalyst for the propargylic substitution of secondary propargylic alcohols with carbon nucleophiles, such as electron-rich arenes, heteroarenes, and 1,3-dicarbony

Al(OTf)3: An efficient recyclable catalyst for direct nucleophilic substitution of the hydroxy group of propargylic alcohols with carbon- and heteroatom-centered nucleophiles to construct C-C, C-O, C-N and C-S bonds

A general and highly efficient Al(OTf)3-catalyzed methodology has been developed for the direct nucleophilic substitution of the hydroxy group in propargylic alcohols with a variety of carbon- and heteroatom-centered nucleophiles such as alcohols, aromatic compounds, amides, and thiols, leading to the construction of C-C, C-O, C-N and C-S bonds.

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

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.