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The radical addition of the Cl-S σ-bond in sulfenyl chlorides to various C-C triple bonds has been achieved with excellent regio- and stereoselectivity in the presence of a catalytic amount of a common iron salt. The reaction is compatible with a variety of functional groups and can be scaled up to the gram-scale with no loss in yield. As well as terminal(More)
Chlorothiolation of terminal alkynes with sulfenyl chlorides yields anti-adducts without transition-metal catalysts. In sharp contrast, transition-metal-catalyzed chlorothiolation has not been developed to date, possibly because organosulfur compounds can poison catalyst. Herein, the regio- and stereoselective palladium-catalyzed chlorothiolation of(More)
Reactions of zirconacyclopentadienes with diethyl ketomalonate gave alpha-pyrans in excellent yields in the presence of BiCl3. In the absence of BiCl3, zirconacyclopentadienes did not react with diethyl ketomalonate. Tetraphenylzirconacyclopentadiene reacted with diethyl ketomalonate in the presence of BiCl3 to give a ring-opening product, dienolic ether,(More)
Multi-substituted pentacenes, such as 1,2,3,4,6,8,9,10,11,13-decasubstituted pentacenes (Type I), 1,2,3,4,6,13-hexasubstituted pentacenes (Type II), 1,2,3,4-tetrasubstituted pentacenes (Type III), and 2,3-disubstituted pentacenes (Type IV), 1,2,3,4,6,11-hexasubstituted naphthacenes (Type V), 1,2,3,4-tetrasubstituted naphthacenes (Type VI), and(More)
Planar chirality: Ring-closing metathesis of 1,2-diallylmetallocenes afforded the corresponding 4,7-dihydroindenyl species in high yields. The metallocenes are planar chiral with two different allylic substituents, and kinetic resolution of the racemic 1,2-diallylmetallocene derivatives was realized by molybdenum-catalyzed asymmetric ring-closing metathesis(More)
Palladium-catalyzed reactions of various 2-bromo-3-exo-methylenecycloalkenes with a stabilized nucleophile were examined. When the carbocycles were nine-membered or larger, the corresponding endocyclic allenes were isolated in excellent yields. In a reaction of the eight-membered cyclic substrate, initial formation of a cycloocta-1,2-diene derivative was(More)
A novel and versatile synthetic method for picene derivatives is developed using the Pd-catalyzed intramolecular double cyclization of the corresponding 2,3-bis[(1Z)-2-phenylethenyl]-1,4-dichlorobenzenes, which are readily prepared by Suzuki-Miyaura cross-coupling reactions of polyhalobenzenes with (Z)-arylethenylboronates. The physical properties of the(More)
A series of picenes having methoxy groups was synthesized through Pd-catalyzed Suzuki-Miyaura couplings or Wittig reaction/intramolecular cyclization sequences, and their physicochemical properties and single-crystal structures were evaluated. The substitution position effects between the outer 1,12-, 2,11-, and 4,9-position and the inner 3,10-position are(More)
Stereocontrolled alkynylzirconation of unactivated alkynes was achieved by the reaction of an alkyne with Cp2ZrEt2 and alkynyl halide in this order. After hydrolysis of the alkynylzirconation product, trisubstituted enyne derivatives were obtained in good yields. Functionalized enynes were also prepared by the reaction of the alkynylzirconation products(More)
A direct selenation of inert C-H bonds of benzamide derivatives and their related compounds with diselenides has been achieved with the palladium catalyst. The reaction was compatible with a variety of functional groups, including a bromo group. Primitive mechanistic insights revealed that the reaction proceeded through a C-H bond cleavage and the(More)