63139-23-1Relevant articles and documents
Anti-carbometalation of alkynyl sulfides using indium tribromide and ketene silyl acetals
Kang, Kyoungmin,Nishimoto, Yoshihiro,Sakamoto, Kosuke,Yasuda, Makoto
supporting information, p. 1136 - 1139 (2020/10/06)
We developed the regioselective anti-carbometalation of alkynyl sulfides via the use of InBr3 and organosilicon nucleophiles to give β-mercaptoalkenylindium compounds. The structure of β-mercaptoalkenylindium was characterized by X-ray crystallographic analysis. A variety of disubstituted alkenyl sulfides were regio- and stereoselectively obtained by either halogenation or Pd-catalyzed cross-coupling with aryl halides using the mercaptoalkenylindiums.
A Short Synthesis of (+)-Brefeldin C through Enantioselective Radical Hydroalkynylation
Gn?gi, Lars,Martz, Severin Vital,Meyer, Daniel,Sch?rer, Robin Marc,Renaud, Philippe
supporting information, p. 11646 - 11649 (2019/08/30)
A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows a high trans diastereoselectivity to be achieved during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis requires six product purifications and it provides (+)-brefeldin C in 18 % overall yield.
Synthesis of aryl α,α-difluoroethyl thioethers a novel structure motif in organic chemistry, and extending to aryl α,α-difluoro oxyethers
Tomita, Ren,Al-Maharik, Nawaf,Rodil, Andrea,Bühl, Michael,O'Hagan, David
supporting information, p. 1113 - 1117 (2018/02/22)
A method for the preparation of aryl α,α-difluoroethyl thioethers (ArSCF2CH3) is reported and the synthesis approach is extended to aryl α,α-difluoroethyl oxygen ethers. Selected building blocks are further elaborated in cross-coupli
Divergent Reactivity of Thioalkynes in Lewis Acid Catalyzed Annulations with Donor–Acceptor Cyclopropanes
Racine, Sophie,Hegedüs, Bence,Scopelliti, Rosario,Waser, Jér?me
supporting information, p. 11997 - 12001 (2016/08/16)
Efficient methods for the convergent synthesis of (poly)cyclic scaffolds are urgently needed in synthetic and medicinal chemistry. Herein, we describe new annulation reactions of thioalkynes with phthalimide-substituted donor–acceptor cyclopropanes, which gave access to highly substituted cyclopentenes and polycyclic ring systems. With silyl-thioalkynes, the Lewis acid catalyzed [3+2] annulation reaction with donor–acceptor cyclopropanes took place to afford 1-thio-cyclopenten-3-amines. On the other hand, an unprecedented polycyclic compound was formed with alkyl-thioalkynes through a reaction pathway directly involving the phthalimide group. The two transformations proceeded in good yields and tolerated a large variety of functional groups.
Facile 1,1-carboboration reactions of acetylenic thioethers
Eller, Christina,Kehr, Gerald,Daniliuc, Constantin G.,Froehlich, Roland,Erker, Gerhard
supporting information, p. 384 - 386 (2013/03/14)
The acetylenic thioether PhSCi - CSPh undergoes a rapid 1,1-carboboration reaction with facile -SPh migration upon treatment with B(C6F5)3 to yield the borylated ketene dithioacetal product (PhS)2C=C(C6/su
Sulfur-substituted tetrahedranes
Ochiai, Tatsumi,Nakamoto, Masaaki,Inagaki, Yusuke,Sekiguchi, Akira
, p. 11504 - 11507 (2011/10/04)
The stable sulfur-substituted tetrahedrane derivatives 2-4 were synthesized by the reaction of tris(trimethylsilyl)tetrahedranyllithium 1 with diphenyl disulfide, bis(4-nitrophenyl) disulfide, and bis(2,4-dinitrophenyl) disulfide, respectively, and characterized by both NMR spectroscopy and X-ray crystallography. Phenylsulfonyltetrahedrane 5 was prepared by the reaction of 2 and m-chloroperbenzoic acid. The UV-vis absorption spectra of 2-4 suggested an interaction of the σ orbital of the tetrahedrane core and the lone-pair electrons on the sulfur atom, whereas no interaction for 5 was found. Thermal reactions of 2 and 5 are also reported; 2 underwent fragmentation into two acetylene molecules, whereas 5 gave the corresponding cyclobutadiene.
Regiocontrolled synthesis of ring-fused thieno[2,3-c]pyrazoles through 1,3-dipolar cycloaddition of nitrile imines with sulfur-based acetylenes
Chandanshive, Jay Zumbar,Bonini, Bianca Flavia,Gentili, Denis,Fochi, Mariafrancesca,Bernardi, Luca,Franchini, Mauro Comes
experimental part, p. 6440 - 6447 (2011/01/13)
1,3-Dipolar cycloadditions of C-carboxymethyl-N-arylnitrile imines with substituted acetylenes bearing thiol or sulfone groups were studied. The sulfur controls the regiochemistry of the reaction, and this protocol was applied to the synthesis of ring-fus
Oxidative addition of Pd(0) to Ar-SO2R bonds: Heck-type reactions of sulfones
Ruano, Jose Luis Garcia,Aleman, Jose,Paredes, Cristina Garcia
, p. 2683 - 2686 (2007/10/03)
Phenyl vinyl sulfones and sulfoxides react with Pd(OAc)2 to form styryl sulfoxides and sulfones according to the first Mizoroki-Heck reaction reported for these thio derivatives. Only sulfones are able to react by using catalytic amounts of Pd
Short and efficient preparation of alkynyl selenides, sulfides and tellurides from terminal alkynes
Bieber, Lothar W.,Da Silva, Margarete F.,Menezes, Paulo H.
, p. 2735 - 2737 (2007/10/03)
Diphenyl diselenide reacts with terminal alkynes at room temperature in DMSO in the presence of catalytic amounts of copper iodide to give good to excellent yields of alkynyl phenyl selenides. The reaction occurs under neutral conditions and the solvent a
Homolytic carbostannylation of alkenes and alkynes with tributylstannyl enolates
Miura, Katsukiyo,Saito, Hiroshi,Fujisawa, Naoki,Wang, Di,Nishikori, Hisashi,Hosomi, Akira
, p. 4055 - 4057 (2007/10/03)
matrix presented In the presence of AIBN, tributylstannyl enolates derived from aromatic ketones reacted with electron-deficient alkenes and a variety of alkynes to give the corresponding carbostannylated adducts. The reactions with methyl acrylate gave α-tributylstannylmethyl-γ-ketoesters, unlike the known Michael-type reaction of stannyl enolates forming δ-ketoesters. The carbostannylation of alkynes proceeded in an anti addition mode to afford β,γ-unsaturated ketones. The reactivity of stannyl enolates as radical transfer agents could be utilized for radical cyclization of 1,6-enynes.