957768-42-2Relevant academic research and scientific papers
Ligand-free (: Z)-selective transfer semihydrogenation of alkynes catalyzed by in situ generated oxidizable copper nanoparticles
Grela, Karol,Kusy, Rafa?
supporting information, p. 5494 - 5502 (2021/08/16)
Herein, we present (Z)-selective transfer semihydrogenation of alkynes based on in situ generated CuNPs in the presence of hydrogen donors, such as ammonia-borane and a green protic solvent. This environmentally friendly method is characterized by operational simplicity combined with high stereo- and chemoselectivity and functional group compatibility. Auto-oxidation of CuNPs after the completion of a semihydrogenation reaction results in the formation of a water-soluble ammonia complex, so that the catalyst may be reused several times by simple phase-separation with no need for any special regeneration processes. Formed NH4B(OR)4 can be easily transformed back into ammonia-borane or into boric acid. In addition, a one-pot tandem sequence involving a Suzuki reaction followed by semihydrogenation was presented, which allows minimization of chemical waste production.
Palladium-catalyzed decarbonylative sonogashira coupling of terminal alkynes with carboxylic acids
Chen, Tieqiao,Huang, Tianzeng,Li, Chunya,Li, Wenhui,Li, Xinyi,Li, Zhaohui,Liu, Long,Tang, Zhi,Zhang, Tao
supporting information, p. 3304 - 3309 (2021/05/31)
A direct decarbonylative Sonogashira coupling of terminal alkynes with carboxylic acids was achieved through palladium catalysis. This reaction did not use overstoichiometric oxidants, thus overcoming the homocoupling issue of terminal alkynes. Under the reaction conditions, a wide range of carboxylic acids including those bioactive ones could couple readily with various terminal alkynes, thus providing a relative general method for preparing internal alkynes.
Gold(I)-Catalyzed Cross-Coupling Reactions of Arenediazonium Salts with Alkynoic Acids
Abrams, J. N.,Chi, B. K.
, p. 1236 - 1244 (2020/09/17)
Abstract: The reaction of simple alkynoate salts with isolated arenediazonium tetrafluoroborate salts that had been pre-conditioned with the gold(I) catalyst AuCl(Me2S) led to the formation of cross-coupled products via a decarboxylative Sonogashira reaction process in modest yield and under mild conditions. The major by-product is a defunctionalized aryl moiety stemming from the diazonium salt, which competitively forms via hydrodediazonation. Good functional group tolerance and reaction site selectivity were attained in this limited investigation.
SO2F2-Mediated Oxidative Dehydrogenation and Dehydration of Alcohols to Alkynes
Zha, Gao-Feng,Fang, Wan-Yin,Li, You-Gui,Leng, Jing,Chen, Xing,Qin, Hua-Li
, p. 17666 - 17673 (2019/01/04)
Direct synthesis of alkynes from inexpensive, abundant alcohols was achieved in high yields (greater than 40 examples, up to 95% yield) through a SO2F2-promoted dehydration and dehydrogenation process. This straightforward transformation of sp3-sp3 (C-C) bonds to sp-sp (C=C) bonds requires only inexpensive and readily available reagents (no transition metals) under mild conditions. The crude alkynes are sufficiently free of impurities to permit direct use in further transformations, as illustrated by regioselective Huisgen alkyne-azide cycloaddition reactions with PhN3 to give 1,4-substituted 1,2,3-traiazoles (16 examples, up to 92% yield) and Sonogashira couplings (10 examples, up to 77% yield).
Palladium-Catalyzed Decarboxylative Coupling Reactions of Propiolic Acid Derivatives and Arylsulfonyl Hydrazide
Park, Jaerim,Song, Kwang Ho,Lee, Sunwoo
, p. 3197 - 3204 (2018/08/12)
Arylsulfonyl hydrazides were employed as coupling partners for the decarboxylative coupling reaction of propiolic acid derivatives. When the reaction was conducted using Pd(TFA) 2 (1.0 mol%), dppp (1.0 mol%), and Cu(OAc) 2 (2.4 equiv
Potassium tert-butoxide-mediated generation of arynes from o-bromoacetophenone derivatives
Chang, Denghu,Gao, Fei,Shi, Lei
, p. 2428 - 2434 (2018/04/24)
o-bromoacetophenone derivatives as new versatile aryne precursors are induced to selectively eliminate the CAr–Br and CAr–C(Ac) bonds in the help of t-BuOK. Furthermore, the active aryne intermediates are successfully appl
Development of a Palladium-Catalyzed Process for the Synthesis of Z-Alkenes by Sequential Sonogashira–Hydrogenation Reaction
Hancker, S?ren,Neumann, Helfried,Beller, Matthias
supporting information, p. 5253 - 5259 (2018/09/14)
A novel and selective sequential one-pot protocol for the synthesis of Z-alkenes via Sonogashira–semihydrogenation is reported. The efficiency of the methodology is increased by utilizing PdCl2/BuPAd2 as homogeneous catalyst for the Sonogashira coupling and subsequently transforming the transition metal complex into a heterogeneous Pd hydrogenation catalyst. This methodology represents one of the rare examples directly combining homogeneous and heterogeneous catalysis.
Palladium-catalyzed decarboxylative coupling reaction with alkynyl carboxylic acids and arylsiloxanes
Jang, Jisun,Raja, Gabriel Charles Edwin,Lee, Ju-Hyeon,Son, Yujeong,Kim, Jimin,Lee, Sunwoo
, p. 4581 - 4584 (2016/09/23)
A decarboxylative coupling reaction for alkynyl carboxylic acids and arylsiloxanes was developed using a palladium catalyst. This method provided the desired coupled products in moderate to good yields by reacting the alkynyl carboxylic acids and arylsiloxanes with Pd(dba)2(1.0?mol?%), 1,1-bis(diphenylphosphino)methane (1.0?mol?%), and AgF2(2.0?equiv) at 60?°C for 6?h.
Nickel-Catalyzed Hiyama-type Decarboxylative Coupling of Propiolic Acids and Organosilanes
Edwin Raja, Gabriel Charles,Irudayanathan, Francis Mariaraj,Kim, Han-Sung,Kim, Jimin,Lee, Sunwoo
, p. 5244 - 5249 (2016/07/06)
A Ni catalytic system was developed for the decarboxylative coupling reaction of alkynyl carboxylic acids with organosilanes. Ni(acac)2 and 1,10-phenanthroline showed the best result in the presence of CsF and CuF2 at 120 °C. This system tolerated the presence of alkyl, alkoxy, halogen, nitro, cyano, ketone, and ester functional groups. Moreover, the reaction with but-2-ynedioic acid and organosilane afforded the corresponding symmetrical diarylalkynes.
