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During the last decade, catalytic functionalization of C–H bonds has become one of the most attractive research areas in modern organic synthesis. To date, many efficient catalytic reactions have been reported. In almost all of these reactions, heteroatom-directed C–H bond cleavage and/or C–C bond formation are quite important for attaining high regioselectivity and efficiency. In this chapter, several...
Regioselectivity was achieved in transition-metal-catalyzed arylation reactions via C–H bond cleavage through the use of chelation-assistance. Palladium, rhodium, and ruthenium complexes proved useful for the development of broadly applicable methodologies for intermolecular direct arylation reactions. These include protocols for direct arylation reactions using aryl chlorides and tosylates as well...
Aromatic compounds having oxygen-containing substituents such as phenols, phenyl ketones, benzyl alcohols, and benzoic acids undergo regioselective arylation and vinylation via C–H bond cleavage in the presence of transition-metal catalysts. The latter two substrates are also arylated and vinylated via C–C bond cleavage accompanied by liberation of ketones and CO2, respectively. Coordination of their...
This chapter describes advances over the past four decades in Pd-mediated and Pd-catalyzed reactions for the highly regioselective oxidative functionalization of C–H bonds. The synthetic utility and the key mechanistic features of both stoichiometric and catalytic C–X (X = O, Cl, Br, I, F, N) bond-forming reactions are presented. The intermediacy of high oxidation state PdIV species in many of these...
Directed metallation of organic molecules is an important tool for the C–C bond activation since this strategy solves the accessibility problem occurring between a metal and a C–C bond that is to be cleaved. Stability of the five-membered metallacyclic complexes derived from the coordinating substrate and transition metal complexes are a driving force for undergoing the C–C bond activation. In this...
Installation of substrate-bound catalyst-directing phosphine groups allows for efficient substrate control of all aspects of reaction selectivity in the course of the industrially important hydroformylation reaction. In particular, the ortho-diphenylphosphanylbenzoyl (o-DPPB) group has proved to be a highly efficient and practical directing group for controlling regioselectivity and diastereoselectivity...
The Mizoroki–Heck reaction is one of the key C–C bond-forming processes in organic synthesis. A prominent variant, which has found broadest application in targeted complex molecule synthesis, is the asymmetric intramolecular Mizoroki–Heck reaction. This methodology has outshone another powerful facet of Mizoroki–Heck chemistry, which has been prospering in recent years, namely directed Mizoroki–Heck...
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