ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTCross-coupling of organosilanes with organic halides mediated by a palladium catalyst and tris(diethylamino)sulfonium difluorotrimethylsilicateYasuo Hatanaka Tamejiro HiyamaCite this: J. Org. Chem. 1988, 53, 4, 918–920Publication Date (Print):February 1, 1988Publication History Published online1 May 2002Published inissue 1 February 1988https://pubs.acs.org/doi/10.1021/jo00239a056https://doi.org/10.1021/jo00239a056research-articleACS...

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTGrignard-type carbonyl addition of allyl halides by means chromous salt. A chemospecific synthesis homoallyl alcoholsYoshitaka Okude, Shigeo Hirano, Tamejiro Hiyama, and Hitosi NozakiCite this: J. Am. Chem. Soc. 1977, 99, 9, 3179–3181Publication Date (Print):April 1, 1977Publication History Published online1 May 2002Published inissue 1 April 1977https://pubs.acs.org/doi/10.1021/ja00451a061https://doi.org/10.1021/ja00451a061research-articleACS...

Abstract There has been extensive research on the development of organic optoelectronic devices, such as light‐emitting diodes, field‐effect transistors, and solid‐state lasers from various viewpoints, ranging basic studies to practical applications. As materials are used solids in these importance chromophores that exhibit intense emissions visible light solid state is greatly increasing field electronics. However, highly efficient emission very difficult attain because most emitting...

Recently, fluorine has become a key element in the remarkable progress of materials and biologically active agents.Since quite unique reactivities properties, chemistry is recognized as being totally different from other halogens.Accordingly, many books reviews have been published.Most them, however, were written by experts specialized fields.Although excellent monographs on organofluorine exist, this new textbook was undertaken with aim overviewing basis organic synthesis.Accordingly,...

The C-2 selective alkenylation of pyridine derivatives is achieved with a catalyst consisting nickel and Lewis acid. Use diorganozinc compounds as the acid gives monoalkenylation products, whereas AlMe3 changes reaction course to afford dienylated which are derived from double insertion alkynes into C(2)−H bond. demonstrates broad substrate scope proceeds high chemo-, regio-, stereoselectivities under mild conditions compared previous examples direct C−H functionalization pyridines.

Direct C-4-selective addition of pyridine across alkenes and alkynes is achieved for the first time by nickel/Lewis acid cooperative catalysis with an N-heterocyclic carbene ligand. A variety substituents on both are tolerated to give linear 4-alkylpyridines in modest good yields. The styrene, other hand, gives branched 4-alkylpyridines. single example alkenylation also described.

Organosilicon compounds act as a nucleophile upon activation by an appropriate base and behave in manner similar to main-group organometallic reagents. In the last decades, structurally divergent organosilicon reagents are available have become more employed for synthetic transformation with aid of transition-metal complexes, because general superior other view stability, solubility, nontoxicity, easy-handling. Particularly, cross-coupling organic halides or pseudohalides has been considered...

Nickel/P(c-C(5)H(9))(3) (PCyp(3)) catalyst effects the addition reactions of fluoroarenes across alkynes, 1,3-dienes, and vinylarenes via activation C-H bonds over C-F bonds. The acidic located ortho to fluorine are exclusively activated afford a range alkenylated alkylated fluoroarenes.

Minimum requirements: Crystals and thin films of 1,4-bis(alkenyl)-2,5-dipiperidinobenzenes, which contain only one benzene ring as the aromatic component, emit visible light with excellent solid-state quantum yields upon irradiation UV light. Polystyrene doped benzenes also exhibit brilliant fluorescence. By modifying alkenyl groups, emission color can be tuned in range from blue to red.

Lewis-acid catalysts such as AlMe3, AlMe2Cl, and BPh3 significantly improve the efficiency of nickel-catalyzed arylcyanation alkynes. Electron-rich aryl cyanides, which exhibit poor reactivity in absence Lewis acids, readily undergo reaction under newly disclosed conditions. Excellent chemoselectivity is observed for cyanides having a chloro bromo group, allowing single-step preparation synthetic intermediate P-3622, squalene synthetase inhibitor. Moreover, first examples alkenyl-...

Organosilicon compounds couple with organic halides or triflates in the presence of a fluoride ion promoter and palladium catalyst. This reaction is general highly chemoselective stereospecific. In addition to carbon-carbon bond formation, carbon-silicon formation realized. Synthetic examples mainly from our Laboratories are reviewed emphasis on mechanism stereochemistry transmetalation silicon palladium. 1. Introduction 2. Cross-Coupling Reactions Alkenylsilanes Organic Halides 3. Dienyne...

Reaction of 1-trimethylsilylalkyne with copper(I) chloride in a polar solvent, DMF, at 60 degrees C under an aerobic conditions smoothly undergoes homo-coupling to give the corresponding symmetrical 1,3-butadiynes 70-99% yields. In addition, (arylethynyl)trimethylsilanes are found couple aryl triflates and chlorides presence Cu(I)/Pd(0) (10 mol %/5 or 10 %) cocatalyst system diarylethynes 49-99% The cross-coupling reaction is applied one-pot synthesis unsymmetrical from...

Nickel complexes having a bulky tri(sec-alkyl)phosphine ligand catalyze hydroheteroarylation of alkynes at 35 degrees C. Selective activation an Ar-H bond over Ar-CN N-protected 3-cyanoindoles is achieved by proper choice and/or N-protecting group. The catalysis applicable to diverse range heteroarenes afford cis-hydroheteroarylation products in highly chemo- and stereoselective manners. Excellent regioselectivity observed with unsymmetrical give the corresponding heteroaryl-substituted...

An alternative to pyridine: Pyridine-N-oxides undergo direct CH activation and add across alkynes under mild nickel catalysis afford (E)-2-alkenylpyridine-N-oxides in modest good yields with high selectivity. Subsequent deoxygenation deoxygenative functionalization proceed smoothly give a wide variety of 2-substituted pyridines. PCyp3=tricyclopentylphosphine, cod=cyclooctadiene.

Abstract

A catalyst system derived from nickel and cocatalytic AlMe2Cl effects the intramolecular arylcyanation of alkenes. The reaction takes place in an exclusive exo-dig manner to give a wide range nitriles having benzylic quaternary carbon good yields. Detailed investigations are described on scope mechanism as well preliminary results asymmetric version provide novel access chiral stereocenters.

A nickel catalyst coordinated by trimethylphosphine is found to effect the addition reaction of Ar-CN bonds in aromatic nitriles across alkynes give rise various beta-arylalkenenitriles.

Regioselective alkenylation and alkylation of 2-pyridone derivatives are achieved through inter- intramolecular insertion alkynes, 1,3-dienes, alkenes into the C(6)−H bond by nickel/AlMe3 catalysis. Coordination heterocycles to Lewis acid cocatalyst their basic carbonyl oxygen is considered be responsible for regioselective activation C−H bonds, probably oxidative addition nickel(0).

ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTOptically Active Polycarbonates: Asymmetric Alternating Copolymerization of Cyclohexene Oxide and Carbon DioxideKyoko Nozaki, Koji Nakano, Tamejiro HiyamaView Author Information Department Material Chemistry Graduate School Engineering, Kyoto University Sakyo-ku, 606-8501, Japan Cite this: J. Am. Chem. Soc. 1999, 121, 47, 11008–11009Publication Date (Web):November 12, 1999Publication History Received12 July 1999Published online12 November...