Naoto Chatani

C-H bonds are ubiquitous in organic compounds. It would, therefore, appear that direct functionalization of substrates by activation of C-H bonds would eliminate the multiple steps and limitations associated with the preparation of functionalized starting materials. Regioselectivity is an important issue because organic molecules can contain a wide variety of C-H bonds. The use of a directing group can largely overcome the issue of regiocontrol by allowing the catalyst to come into proximity wit

During the past decades, synthetic organic chemistry discovered that directing group assisted C-H activation is a key tool for the expedient and siteselective construction of C-C bonds. Among the various directing group strategies, bidentate directing groups are now recognized as one of the most efficient devices for the selective functionalization of certain positions due to fact that its metal center permits fine, tunable, and reversible coordination. The family of bidentate directing groups p

Abstract C‐H‐Bindungen sind in organischen Verbindungen allgegenwärtig. Daher erscheint die direkte Funktionalisierung von Substraten durch Aktivierung von C‐H‐Bindungen als eine gute Strategie, weil so die Herstellung funktionalisierter Ausgangsstoffe vermieden werden kann. Wichtig ist hierbei der Aspekt der Regioselektivität, da organische Moleküle viele C‐H‐Bindungen enthalten können. Erzielt werden kann eine solche Regiokontrolle durch die Verwendung einer dirigierenden Gruppe, die den Katal

The catalytic reactions that involve the cleavage of C-CN bonds and carbon-carbon triple bonds are described in this tutorial review. Regarding the cleavage of a C-CN bond, the catalytic reaction can proceed by two different mechanisms: oxidative addition and deinsertion of silyl isocyanide. A carbon-carbon triple bond can be cleaved in the absence of an organic promoter via the formation of unique organometallic species, such as allenylidene and cyclopropyl carbenoid complexes.

In recent years, transition-metal-catalyzed C-H activation has become a key strategy in the field of organic synthesis. Rhodium complexes are widely used as catalysts in a variety of C-H functionalization reactions because of their high reactivity and selectivity. The availability of a number of rhodium complexes in various oxidation states enables diverse reaction patterns to be obtained. Regioselectivity, an important issue in C-H activation chemistry, can be accomplished by using a directing

Catalytic reactions which involve the cleavage of an sp(3) C-H bond adjacent to a nitrogen atom in N-2-pyridynyl alkylamines are described. The use of Ru(3)(CO)(12) as the catalyst results in the addition of the sp(3) C-H bond across the alkene bond to give the coupling products. A variety of alkenes, including terminal, internal, and cyclic alkenes, can be used for the coupling reaction. The presence of directing groups, such as pyridine, pyrimidine, and an oxazoline ring, on the nitrogen of th

Where HAS you been? A manganese-mediated annulation of 2-isocyanobiaryls with organoboronic acids is developed for the synthesis of a broad range of phenanthridine derivatives. Mechanistic studies indicate that the reaction proceeds by the intramolecular homolytic aromatic substitution (HAS) of an imidoyl radical intermediate.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTHighly Selective Skeletal Reorganization of 1,6- and 1,7-Enynes to 1-Vinylcycloalkenes Catalyzed by [RuCl2(CO)3]2Naoto Chatani, Tsumoru Morimoto, Toyoshige Muto, and Shinji MuraiCite this: J. Am. Chem. Soc. 1994, 116, 13, 6049–6050Publication Date (Print):June 1, 1994Publication History Published online1 May 2002Published inissue 1 June 1994https://pubs.acs.org/doi/10.1021/ja00092a098https://doi.org/10.1021/ja00092a098research-articleACS PublicationsRe

The treatment of 1,6- and 1,7-enynes with a catalytic amount of PtCl2 in toluene at 80 °C results in skeletal reorganization (cyclorearrangement) of the enynes to give 1-vinylcycloalkenes in high yields. A deuterium labeling experiment indicates that two mechanistic paths are operating for the cyclorearrangement. The nature and position of substituents affect the reaction course. Anomalous carbon−carbon bond formation is attained selectively in the reaction of 1,6-enynes having an ester group at

Skeletal reorganization of enynes was studied by electrophilic activation of alkynes with various metal catalysts; the products obtained can be classified into two types, one involving carbon-carbon bond single cleavage (type I) and the other involving carbon-carbon bond double cleavage (type II). Summarized in this review are our studies of the catalytic skeletal reorganization of enynes through the electrophilic activation of alkynes, and recent results from selective formation of type II prod

ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTCarbonylation at sp3 C−H Bonds Adjacent to a Nitrogen Atom in Alkylamines Catalyzed by Rhodium ComplexesNaoto Chatani, Taku Asaumi, Tsutomu Ikeda, Shuhei Yorimitsu, Yutaka Ishii, Fumitoshi Kakiuchi, and Shinji MuraiView Author Information Department of Applied Chemistry Faculty of Engineering, Osaka University Suita, Osaka 565-0871, Japan Cite this: J. Am. Chem. Soc. 2000, 122, 51, 12882–12883Publication Date (Web):December 27, 2000Publication Hi

A new chelation assisted reaction using a removable 8-aminoquinoline bidentate directing group that permits the ruthenium-catalyzed ortho-C–H bond alkylation of aromatic amides with various α,β-unsaturated ketones under straightforward conditions has been developed. This methodology represents the first efficient utilization of enones in the ortho directed ruthenium-catalyzed addition of C–H bonds to C–C double bonds. The reaction offers a broad scope and a high functional group tolerance.