6366-06-9Relevant articles and documents
Synthesis of Phenanthrenes via Palladium-Catalyzed Three-Component Domino Reaction of Aryl Iodides, Internal Alkynes, and o-Bromobenzoic Acids
Deng, Guobo,Liang, Yun,Luo, Xiai,Yang, Xiumei,Yang, Yuan,Yang, Yuzhong,Zhou, Liwei
, p. 1223 - 1230 (2020/04/15)
A new palladium-catalyzed domino alkyne insertion/C-H activation/decarboxylation sequence has been developed, which provides an efficient approach for synthesizing a variety of functionalized phenanthrenes in moderate to good yields. The method shows broad substrate scope and good functional group tolerance by employing readily available materials, including aryl iodides, internal alkynes, and o-bromobenzoic acids, as three-component coupling partners.
Chiral 1,3-diaryl imidazolium salt carbene precursor, synthesis method thereof, metal salt compound and application
-
, (2019/06/07)
The invention discloses a chiral 1,3-diaryl imidazolium salt carbene precursor, a synthesis method thereof, a metal salt compound and application. The chiral 1,3-diaryl imidazolium salt carbene precursor forms a complex together with the copper to catalyz
Calcium carbide catalytically activated with tetra-: N -butyl ammonium fluoride for Sonogashira cross coupling reactions
Hosseini, Abolfazl,Pilevar, Afsaneh,Hogan, Eimear,Mogwitz, Boris,Schulze, Anne S.,Schreiner, Peter R.
, p. 6800 - 6807 (2017/08/22)
We report a novel method for the direct synthesis of mono- and bis-arylated alkynes utilizing catalytically activated CaC2 as the alkyne component. This fluoride-activated cross coupling reaction provides advantages over existing methods regarding operational simplicity, use of readily available starting materials, and low cost.
Iron-Catalyzed Radical Decarboxylative Oxyalkylation of Terminal Alkynes with Alkyl Peroxides
Zhu, Xiaotao,Ye, Changqing,Li, Yajun,Bao, Hongli
supporting information, p. 10254 - 10258 (2017/08/07)
An iron-catalyzed oxyalkylation of alkynes with alkyl peroxides as the alkylating reagents has been investigated. Alkyl peroxides are readily available from aliphatic acids and serve simultaneously as the alkylating reagents and internal oxidants. Primary, secondary, and tertiary alkyl groups of aliphatic acids were readily incorporated into C?C triple bonds and diverse α-alkylated ketones were synthesized. Mechanism studies revealed that this reaction involves highly reactive alkyl free radicals. A unique equilibrium between lauric acid and water catalyzed by the iron(III) catalyst was observed.
The Synthesis of Certain Phomentrioloxin A Analogues and Their Evaluation as Herbicidal Agents
Taher, Ehab S.,Guest, Prue,Benton, Amanda,Ma, Xinghua,Banwell, Martin G.,Willis, Anthony C.,Seiser, Tobias,Newton, Trevor W.,Hutzler, Johannes
, p. 211 - 233 (2017/04/26)
A series of 28 analogues of the phytotoxic geranylcyclohexentriol (-)-phomentrioloxin A (1) has been synthesized through cross-couplings of various enantiomerically pure haloconduritols or certain deoxygenated derivatives with either terminal alkynes or borylated alkenes. Some of these analogues display modest herbicidal activities, and physiological profiling studies suggest that analogue 4 inhibits photosystem II in isolated thylakoids in vitro.
Three-component asymmetric catalytic ugi reaction - Concinnity from diversity by substrate-mediated catalyst assembly
Zhao, Wenjun,Huang, Li,Guan, Yong,Wulff, William D.
, p. 3436 - 3441 (2014/04/03)
The first chiral catalyst for the three-component Ugi reaction was identified as a result of a screen of a large set of different BOROX catalysts. The BOROX catalysts were assembled in situ from a chiral biaryl ligand, an amine, water, BH3×SMe2, and an alcohol or phenol. The catalyst screen included 13 different ligands, 12 amines, and 47 alcohols or phenols. The optimal catalyst system (LAP 8-5-47) provided α-amino amides from an aldehyde, a secondary amine, and an isonitrile with excellent asymmetric induction. The catalytically active species is proposed to be an ion pair that consists of the chiral boroxinate anion and an iminium cation. Harmonious arrangement of parts: A screen of BOROX catalysts that were generated in situ from 13 different ligands and 47 alcohols led to the identification of an effective combination for the catalytic asymmetric three-component Ugi reaction. Experimental results suggest that the catalyst is a chiral polyborate anion, which then forms an ion pair with the iminium cation that is generated from aldehyde and secondary amine.
Aerobic oxidation in nanomicelles of aryl alkynes, in water at room temperature
Handa, Sachin,Fennewald, James C.,Lipshutz, Bruce H.
supporting information, p. 3432 - 3435 (2014/04/03)
On the basis of the far higher solubility of oxygen gas inside the hydrocarbon core of nanomicelles, metal and peroxide free aerobic oxidation of aryl alkynes to β-ketosulfones has been achieved in water at room temperature. Many examples are offered that illustrate broad functional group tolerance. The overall process is environmentally friendly, documented by the associated low E Factors. It's all happenin' in the micelle! The highly preferential dissolution of oxygen gas within the lipophilic cores inside nanomicelles leads to efficient trapping of in situ generated vinyl radicals. These intermediate radicals, derived from arylalkynes and sulfinic acids, lead to β-ketosulfone products, formed under especially mild and green conditions: no metals, no heating or cooling, recyclable aqueous media, and low E Factors.
K3PO4-KOH mixture as efficient reagent for the deprotection of 4-aryl-2-methyl-3-butyn-2-ols to terminal acetylenes
Smeyanov, Alexey,Schmidt, Andreas
, p. 2809 - 2816 (2013/08/23)
A mixture of potassium hydroxide and potassium phosphate was found to be an active reagent mixture for the cleavage of 2-hydroxypropyl-protected acetylenes. The reaction was performed in toluene at reflux temperature and gave terminal acetylenes in good to excellent yields within very short periods of time. Numerous other functional groups are tolerated. Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for full experimental and spectral details.
Synthesis of polysubstituted benzofuran derivatives as novel inhibitors of parasitic growth
Thévenin, Marion,Thoret, Sylviane,Grellier, Philippe,Dubois, Jo?lle
, p. 4885 - 4892 (2013/09/02)
A series of polysubstituted benzofuran derivatives was easily and rapidly prepared using a tandem Sonogashira coupling/cyclization reaction. Subsequent acylation afforded a small library of 39 new compounds that were assayed in cellulo on Plasmodium falci
Palladium(II)-catalyzed heterocyclisation of 8-arylethynyl-1,2,3,4- tetrahydroquinolines: A facile route to 2-aryl-5,6-dihydro-4H-pyrrolo[3,2,1-ij] quinoline derivatives
Marchand, Pascal,Puget, Alain,Le Baut, Guillaume,Emig, Peter,Czech, Michael,Günther, Eckhard
, p. 4035 - 4041 (2007/10/03)
Dihydropyrroloquinolines have been synthesized reacting 8-arylethynyl-1,2,3,4-tetrahydroquinolines in the presence of palladium(II) chloride catalyst. Heteroannulation has been achieved in good yields and tolerates substituents on the tetrahydroquinoline,
