By Fumitoshi Kakiuchi (auth.), Naoto Chatani (eds.)
Directed metalation is well-known as some of the most beneficial methodologies for the regio- and stereoselective new release of organometallic species, the new release of which inevitably ends up in the selective formation of natural items. Cyclometalation utilizing Li, Mn, and Pd, and directed hydrometalation and carbometalation utilizing Al and Zn, were applied for regio- and/or stereoselective synthesis for many years. lately, a brand new chelation-assisted method has been constructed not just for controlling regio- and stereoselectivity of reactions, but in addition for accelerating reactions. particularly, chelation-methodology has been applied as a brand new activation technique, during which a carbon-metal bond is generated without delay from a C-H bond; a response hardly completed utilizing traditional equipment. a wide selection of catalytic functionalization reactions of C-H bonds through the usage of a chelation, were built lately and are comprehensively mentioned during this booklet by way of major specialists. moreover, new methods to directed hydrometalation and directed carbometalation as a key step also are mentioned. a different stereo- and regioselective hydroformylation has been built throughout the usage of directed hydrometalation. The regioselective Mizoroki-Heck response is one other instance within which directed carbometalation can be utilized to accomplish a excessive regioselectivity. those examples emphasize how those cutting edge methodologies are contributing to diverse fields of chemistry.
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Additional resources for Directed Metallation
Intermolecular Arylations of Heterocycles . . . . . . Intermolecular Arylations of Carbocycles and Acyclic Substrates Oxidative Arylation Reactions . . . . . . . . . . . . 2 Rhodium-Catalyzed Arylation Reactions . . . . . . . . . . Arylations with Aromatic Organometallic Reagents . . . . . . . Arylations with Aryl Halides . . . . . . . . . . . . . 2 Ruthenium-Catalyzed Arylation Reactions . . . . . . . . . Arylations with Aromatic Organometallic Reagents .
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This regioselectivity indicates the possibility of π-coordination of the CN group to the ruthenium in the catalytic cycle. Equation 38 Alkenylation of C – H bonds in heteroarenes such as indols, benzimidazoles, and thiazoles with acetylenes takes place with the aid of Ni(cod)2 /PCyp3 catalyst (Eq. 39) . In these cases, the C – H bonds α to Equation 39 30 F. Kakiuchi the heteroatom add to the C – C triple bonds in syn fashion. The role of the directing group such as nitrile and ester groups in this catalytic reaction is a matter of some dispute, but this regio- and stereoselective alkenylation of heteroaromatic compounds provides a new protocol for functionalization of unreactive C – H bonds.