- Palladium-catalyzed decarbonylative sonogashira coupling of terminal alkynes with carboxylic acids
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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.
- Chen, Tieqiao,Huang, Tianzeng,Li, Chunya,Li, Wenhui,Li, Xinyi,Li, Zhaohui,Liu, Long,Tang, Zhi,Zhang, Tao
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supporting information
p. 3304 - 3309
(2021/05/31)
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- Ligand-free (: Z)-selective transfer semihydrogenation of alkynes catalyzed by in situ generated oxidizable copper nanoparticles
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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.
- Grela, Karol,Kusy, Rafa?
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supporting information
p. 5494 - 5502
(2021/08/16)
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- Gold(I)-Catalyzed Cross-Coupling Reactions of Arenediazonium Salts with Alkynoic Acids
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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.
- Abrams, J. N.,Chi, B. K.
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p. 1236 - 1244
(2020/09/17)
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- SO2F2-Mediated Oxidative Dehydrogenation and Dehydration of Alcohols to Alkynes
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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).
- Zha, Gao-Feng,Fang, Wan-Yin,Li, You-Gui,Leng, Jing,Chen, Xing,Qin, Hua-Li
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p. 17666 - 17673
(2019/01/04)
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- Palladium-Catalyzed Decarboxylative Coupling Reactions of Propiolic Acid Derivatives and Arylsulfonyl Hydrazide
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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
- Park, Jaerim,Song, Kwang Ho,Lee, Sunwoo
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p. 3197 - 3204
(2018/08/12)
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- Potassium tert-butoxide-mediated generation of arynes from o-bromoacetophenone derivatives
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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
- Chang, Denghu,Gao, Fei,Shi, Lei
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p. 2428 - 2434
(2018/04/24)
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- Development of a Palladium-Catalyzed Process for the Synthesis of Z-Alkenes by Sequential Sonogashira–Hydrogenation Reaction
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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.
- Hancker, S?ren,Neumann, Helfried,Beller, Matthias
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supporting information
p. 5253 - 5259
(2018/09/14)
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- Palladium-catalyzed decarboxylative coupling reaction with alkynyl carboxylic acids and arylsiloxanes
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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.
- Jang, Jisun,Raja, Gabriel Charles Edwin,Lee, Ju-Hyeon,Son, Yujeong,Kim, Jimin,Lee, Sunwoo
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p. 4581 - 4584
(2016/09/23)
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- Nickel-Catalyzed Hiyama-type Decarboxylative Coupling of Propiolic Acids and Organosilanes
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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.
- Edwin Raja, Gabriel Charles,Irudayanathan, Francis Mariaraj,Kim, Han-Sung,Kim, Jimin,Lee, Sunwoo
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p. 5244 - 5249
(2016/07/06)
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- Palladacycle-catalyzed deacetonative sonogashira coupling of aryl propargyl alcohols with aryl chlorides
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An efficient and general protocol for the deacetonative Sonogashira coupling of aryl propargyl alcohols with aryl chlorides is described. The reaction proceeded smoothly with the catalyst system of palladacycle/Xphos. This result represents the first succ
- Hu, Hao,Yang, Fan,Wu, Yangjie
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p. 10506 - 10511
(2013/11/06)
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- Phosphine-free palladium-catalyzed decarboxylative coupling of alkynylcarboxylic acids with aryl and heteroaryl halides
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We herein report the design and development of a carboxyamido/carbene ligand and its Pd-complex for the decarboxylative coupling of alkynylcarboxylic acids with aryl and heteroaryl halides to afford arylalkynes. Copyright
- Reddy, Police Vishnuvardhan,Srinivas, Pottabathula,Annapurna, Manne,Bhargava, Suresh,Wagler, Jorg,Mirzadeh, Nedaossadat,Kantam, Mannepalli Lakshmi
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supporting information
p. 705 - 710
(2013/04/23)
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- Iron-catalyzed cross-coupling between 1-bromoalkynes and grignard-derived organocuprate reagents
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An efficient iron-catalyzed cross-coupling reaction between alkynyl bromides and Grignard-derived organocuprates has been developed. A series of alkynylarenes were successfully synthesised by starting from different 1-bromoalkynes and Grignard reagents. The methodology was successfully used for the two-step stereoselective synthesis of combretastatins and represents a valid alternative to the classical syntheses of alkynylarenes.
- Castagnolo, Daniele,Botta, Maurizio
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supporting information; experimental part
p. 3224 - 3228
(2010/08/20)
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- Gold-catalyzed halogenation of aromatics by N-halosuccinimides
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(Chemical Equation Presented) Golden bromination: A highly efficient and mild AuCl3-catalyzed bromination of aromatic rings with Nbromosuccinimide (NBS) has been developed. This method works with a low catalyst loading (down to 0.01 mol %) and can be combined with transition metal catalyzed transformations to deliver various aryl products.
- Mo, Fanyang,Yan, Jerry Mingtao,Qiu, Di,Li, Fei,Zhang, Yan,Wang, Jianbo
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scheme or table
p. 2028 - 2032
(2010/06/17)
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- Palladium-catalyzed decarboxylative coupling of alkynyl carboxylic acids and aryl halides
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2-Octynoic acid and phenylpropiolic acid were employed for the palladium-catalyzed decarboxylative coupling reaction and with a variety of aryl halides. The former needed 1,4-bis(diphenylphosphino)butane (dppb) as a ligand and the latter tri-tert-butylpho
- Moon, Jeongju,Jang, Mihee,Lee, Sunwoo
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supporting information; experimental part
p. 1403 - 1406
(2009/07/04)
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