Kiyohiko Nakajima

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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)
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)
Photoreactivities of Ni(II)- and Pt(II)-hydrazone complexes, [NiCl(L)] (Ni1) and [PtCl(L)] (Pt1), respectively [HL = 2-(diphenylphosphino)benzaldehyde-2-pyridylhydrazone], were investigated in detail via UV-vis absorption, (1)H nuclear magnetic resonance (NMR) spectroscopy, and electrospray ionization time-of-flight (ESI-TOF) mass spectrometry; the two(More)
Two one-pot multicomponent synthetic methods for highly substituted indenes are described. The intermolecular coupling of aromatic ketones with alkynes on low-valent zirconocene species generates oxazirconacyclopentenes, which upon hydrolysis with 20% HCl for 3 h afforded indene derivatives in good to excellent yields. Similarly, the pair-selective coupling(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)