37559-19-6Relevant academic research and scientific papers
Base-Free Synthesis and Synthetic Applications of Novel 3-(Organochalcogenyl)prop-2-yn-1-yl Esters: Promising Anticancer Agents
Gritzenco, Fabiane,Kazmierczak, Jean C.,Anjos, Thiago,Speran?a, Adriane,Peixoto, Maura L. B.,Godoi, Marcelo,Ledebuhr, Kauane N. B.,Brüning, César Augusto,Zamin, Lauren L.,Godoi, Benhur
, p. 2676 - 2688 (2021/05/06)
This manuscript portrays the CuI-catalyzed Csp-chalcogen bond formation through cross-coupling reactions of propynyl esters and diorganyl dichalcogenides by using DMSO as solvent, at room temperature, under base-free and open-to-air atmosphere conditions.
Metal-Free Regioselective Chloroazidation of Internal Alkynes
Huang, Bin,Liffert, Raphael,Linden, Anthony,Gademann, Karl
supporting information, p. 981 - 984 (2019/01/04)
A metal-free, room temperature protocol for the regioselective chloroazidation of internal alkynes is disclosed. The reactions of internal alkynes with trimethylsilyl azide (TMSN3) in the presence of 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) afforded the corresponding chloroazidoalkenes in good yields. This reaction has good functional group tolerance and is operationally simple.
Sonogashira reaction using arylsulfonium salts as cross-coupling partners
Tian, Ze-Yu,Wang, Shi-Meng,Jia, Su-Jiao,Song, Hai-Xia,Zhang, Cheng-Pan
, p. 5454 - 5457 (2017/11/06)
Triarylsulfonium, alkyl- and fluoroalkyl(diaryl)-sulfonium, and aryl(dialkyl)sulfonium triflates are successfully used as a new family of cross-coupling participants in the Sonogashira reaction as aryldiazonium, diaryliodonium, and tetraphenylphosphonium salts. It was found that terminal alkynes reacted mildly with triarylsulfonium or (2,2,2-trifluoroethyl)diphenylsulfonium triflate at room temperature under Pdand Cu-cocatalysis to give the corresponding arylalkynes in up to >99% yield. This protocol represents the first use of arylsulfonium salts as cross-coupling partners in the Pd/Cu-catalyzed Sonogashira reaction.
Synthesis of α-acyloxyketone derivatives via the platinum-catalyzed migration of propargylic esters
Tsukano, Chihiro,Yamamoto, Sho,Takemoto, Yoshiji
, p. 710 - 719 (2015/11/27)
The synthesis of α-acyloxyketones via the migration of a propargylic ester followed by the intramolecular nucleophilic addition of the resulting allene was achieved using a cationic platinum catalyst. The optimized conditions for this transformation were
Palladium-catalyzed oxidative carbonylative coupling of arylboronic acids with terminal alkynes to alkynones
Natte, Kishore,Chen, Jianbin,Neumann, Helfried,Beller, Matthias,Wu, Xiao-Feng
supporting information, p. 5590 - 5593 (2014/07/22)
We describe here an interesting palladium-catalyzed oxidative carbonylation of arylboronic acids with terminal alkynes. By the appropriate combination of a palladium salt, a ligand, and an oxidant, the desired alkynones were isolated in moderate to good yields. Notably, all the reactions were performed at room temperature, and moisture and air can be tolerated by this procedure. More importantly, this is the first example of oxidative carbonylative coupling of arylboronic acids with alkynes which filled the missing link in carbonylative coupling reactions. the Partner Organisations 2014.
Zn(OTf)2-promoted chemoselective esterification of hydroxyl group bearing carboxylic acids
Mamidi, Narsimha,Manna, Debasis
, p. 2386 - 2396 (2013/05/21)
Selective esterification of aliphatic and aromatic carboxylic acids with various alcohols is studied using triphenylphosphine, I2, and a catalytic amount of Zn(OTf)2. Use of this catalyst allows the formation of esters at a faster rate with good to excellent yield by activating the in situ generated acyloxyphosphonium ion intermediate. During the esterification process, both their aromatic and aliphatic hydroxyl groups are fully preserved from transesterification. The results show that the bulkiness and the reactivity of this doubly activated intermediate III control the selectivity and the rate of the reaction, respectively. The method is also useful for direct amidation reactions.
Combining oxidative N-heterocyclic carbene catalysis with click chemistry: A facile one-pot approach to 1,2,3-triazole derivatives
Ramanjaneyulu,Reddy, Virsinha,Arde, Panjab,Mahesh, Sriram,Anand, R. Vijaya
, p. 1489 - 1496 (2013/07/26)
A combination of the oxidative N-heterocyclic carbene catalysis and click chemistry has been explored for the direct, one-pot synthesis of 1,2,3-triazole derivatives from aromatic aldehydes. This procedure was found to be very efficient and a variety of 1
Copper(I)-catalyzed regio- and chemoselective single and double addition of nucleophilic silicon to propargylic chlorides and phosphates
Hazra, Chinmoy K.,Oestreich, Martin
supporting information; experimental part, p. 4010 - 4013 (2012/10/08)
Copper(I)-catalyzed propargylic substitution of linear precursors with (Me2PhSi)2Zn predominantly yields the γ isomer independent of the propargylic leaving group. The thus formed allenylic silane reacts regioselectively with another equivalent of (Me2PhSi) 2Zn, yielding a bifunctional building block with allylic and vinylic silicon groups. The reaction rates of both steps are well-balanced for chloride (γ:α ≥ 99:1) where the propargylic displacement occurs quantitatively prior to the addition step. Substitutions of α-branched propargylic phosphates are also reported.
Palladium-catalyzed Sonogashira reactions of aryl amines with alkynes via in situ formation of arenediazonium salts
Wu, Xiao-Feng,Neumann, Helfried,Beller, Matthias
supporting information; experimental part, p. 7959 - 7961 (2011/08/05)
A general and convenient palladium-catalyzed Sonogashira reaction of in situ generated arenediazonium salts has been developed and various internal arylalkynes are produced in good yields under mild conditions.
