208347-79-9Relevant articles and documents
A new synthesis of combretastatins A-4 and AVE-8062A
Lara-Ochoa, Francisco,Espinosa-Pérez, Georgina
, p. 7007 - 7010 (2007)
Combretastatins A-4 and AVE-8062A have been synthesized by coupling 3,4,5-trimethoxyphenylacetylene with the corresponding iodomethoxyphenol and bromomethoxyaniline, followed by hydrolysis of the thermally-stable Ti(II)-alkyne complexes.
Expanding the oxidative chemistry of organocopper reagents: Facile oxidative cross-coupling of copper acetylides with arylboronic acids
Verna, Florian,Guissart, Celine,Pous, Jonathan,Evano, Gwilherm
, p. 523 - 529 (2013)
We have developed an efficient procedure for oxidative cross-coupling between arylboronic acids and alkynylcopper reagents. Upon simple addition of 1,10-phenanthroline in the presence of oxygen, these highly stable, readily available polymeric reagents are easily activated and transfer their alkynyl group after subsequent transmetallation with the boronic acid. These results further expand the oxidative chemistry of organocopper compounds together with providing a user-friendly entry to diaryl acetylenes.
N-Heterocyclic carbene-Pd(II)-PPh3 complexes as a new highly efficient catalyst system for the Sonogashira cross-coupling reaction: Synthesis, characterization and biological activities
Boubakri,Mansour,Harrath,?zdemir,Ya?ar,Hamdi
, p. 183 - 199 (2018)
A novel series of N-heterocyclic carbene-phosphine palladium(II) complexes has been synthesized and fully characterized by IR, 1H NMR, 13C NMR, and 31P NMR spectroscopies, and elemental analysis. The new N-heterocyclic car
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.
Palladium-catalyzed alkynylation of aromatic amines via in situ formed trimethylammonium salts
Chen, Tieqiao,Huang, Tianzeng,Liu, Long,Yu, Wen-Qing
supporting information, (2020/02/04)
A palladium-catalyzed alkynylation of aromatic amines with terminal alkynes via in situ formed trimethylammonium salts is developed. Compared with previous system using ammonium salts as starting materials and high loading of pre-prepared NHC-Pd catalyst (10 mol% Pd), this reaction directly employed amines as the coupling partners and the commercially available Pd2(dba)3/PPh2Cy (1 mol% Pd) as the catalyst, greatly simplifying the manipulation and decreasing the cost.
DBU-Mediated Synthesis of Aryl Acetylenes or 1-Bromoethynylarenes from Aldehydes
Thummala, Yadagiri,Karunakar, Galla V.,Doddi, Venkata Ramana
, p. 611 - 616 (2019/01/04)
Two well known synthetic organic reactions Ramirez olefination and Corey-fuchs reactions are integrated in one-pot sequential manner for the synthesis of arylacetylenes and 1,3-enynes starting directly from commercially available aldehydes. The bicyclic amidine 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) along with additive NaOH not only exclusively afforded the terminal alkynes directly from the aldehydes, but also enhanced the reaction rate. The dynamic nature of DBU also facilitated the isolation of 1-bromoalkynes intermediate products. Selection of additive from NaOH and H2O served as a switch for the synthesis of terminal alkyne and 1-bromoalkynes, respectively. (Figure presented.).
DBU-Mediated Efficient Synthesis of Diaryl Ethynes and Enynes from 1,1-Dibromoalkenes at Room Temperature
Thummala, Yadagiri,Morri, Ashok K.,Karunakar, Galla V.,Doddi, Venkata Ramana
, p. 6280 - 6285 (2018/11/23)
The reaction of 1,1-dibromoalkenes and aryl iodides in the presence of DBU and a PdII/CuI catalytic system afforded diaryl alkynes and enynes at ambient temperature. Control experiments demonstrated the essential ligand role of DBU i
Sonogashira cross-coupling reaction catalyzed by N-heterocyclic carbene-Pd(II)-PPh3 complexes under copper free and aerobic conditions
Dehimat, Zineb Imene,Ya?ar, Sedat,Tebbani, Dahmane,?zdemir, ?smail
, p. 325 - 334 (2017/09/29)
NHC-Pd-PPh3 complexes with the bulky benzyladamantyl substited N-heterocyclic carbene (NHC) were synthesized and characterised by NMR, HRMS and micro analyse. These complexes were proceeded to Sonogashira-Hagihara coupling reaction between aryl
Sonogashira cross-coupling reaction catalysed by mixed NHC-Pd-PPh3 complexes under copper free conditions
Touj, Nedra,Ya?ar, Sedat,?zdemir, Nam?k,Hamdi, Naceur,?zdemir, ?smail
, p. 59 - 71 (2018/02/27)
Mixed NHC–Pd–PPh3 complexes with a methoxyethyl-substituted N-heterocyclic carbene (NHC) were synthesised and characterised by NMR, HRMS, elemental analysis and X-ray crystallography for complex 3b. These complexes were applied to Sonogashira c
Synthesis and catalytic applications of palladium N-heterocyclic carbene complexes as efficient pre-catalysts for Suzuki-Miyaura and Sonogashira coupling reactions
Boubakri,Yasar,Dorcet,Roisnel,Bruneau,Hamdi,Ozdemir
, p. 5105 - 5113 (2017/07/11)
A new palladium complex series with N-heterocyclic carbene (NHC), pyridine and phosphine ligands, PdCl2(L)NHC (2a-c)(L = NHC), PdCl2(L1)NHC(3a-c)(L1 = pyridine), PdCl2(L2)NHC(4a-c)(L2 = triphenylphosphine) was synthesised and fully characterized. The catalytic activities of these complexes were screened for the Sonogashira and Suzuki-Miyaura reactions between arylhalides and phenylacetylene, and phenylboronic acid, respectively. The results pointed out that the carbene/phosphine complexes 4a-c exhibited excellent catalytic activities as compared to 2a-c, 3a-c, and the well-known systems for the palladium-catalysed Sonogashira reaction. The reactivity of 4a-c in these preliminary Sonogashira coupling tests seems to be higher than that of previously reported catalytic systems based on Pd(NHC) moieties. These new palladium NHC complexes are among the first reported palladium catalysts that are efficient for catalysing the Sonogashira reaction from arylchloride substrates.
