Handbook of C-H transformations: applications in organic synthesis

Abstract

Volume 1. Preface. List of Contributors. I. General. 1. What is C-H Bond Activation? (Bengu Sezen and Dalibor Sames). 1.1 Introduction. 1.2 Activation or 1.3 The Origin and Historical Context of the Organometallic Definition. 1.4 What Do We Do With Two Definitions? 1.5 Conclusion. 2. C-H Transformation in Industrial Processes (Leslaw Mleczko, Sigurd Buchholz, Christian Munnich) 2.1 Introduction. 2.2 Alkane Activation. 2.3 C-H Transformation at Olefins. 2.4 Basic Chemicals from Aromatic Hydrocarbons. 2.5 Fine Chemicals. II. C-H Transformation at sp-Hybridized Carbon Atoms. 1. C-H Transformation at Terminal Alkynes. 1.1 Recent Developments in Enantioselective Addition of Terminal Alkynes to Aldehydes (Tobias Ritter and Erick M. Carreira). 1.2 The Sonogashira Coupling Reaction (Herbert Plenio and Anupama Datta). 1.3 Glaser Homocoupling and the Cadiot-Chodkiewicz Heterocoupling Reaction (Peter Siemsen and Beatrice Felber). 1.4 Dimerization of Terminal Alkynes (Emilio Bustelo and Pierre H. Dixneuf). 1.5 anti -Markovnikov Addition to Terminal Alkynes via Ruthenium Vinylidene Intermediates (Christian Bruneau). 2. Asymmetric Hydrocyanation of Alkenes (Jos Wilting and Dieter Vogt). 2.1 Introduction. 2.2 Mechanism. III. C-H Transformation at sp 2 -hybridized Carbon Atoms. 1. C-H Transformations at Arenes. 1.1 Direct Oxidation of Arenes to Phenols and Quinones (Vsevolod V. Rostovtsev). 1.2 Metalation of Arenes. 1.3 Alkylation and Vinylation of Arenes. 1.4 Aryl-Aryl Coupling Reactions. 2. C-H Transformation at Alkenes. 2.1 The Heck Reaction (Lukas Gooben and Kathe Baumann). 2.2 Wacker Oxidation (Lukas Hintermann). 3. C-H Transformation at Aldehydes and Imines. 3.1 Inter- and Intramolecular Hydroacylation (Chul-Ho Jun and Young Jun Park). Volume 2. IV. C-H Transformation at sp 3 -hybridized Carbon Atoms. 1. C-H Transformation at Functionalized Alkanes. 1.1 C-H Transformation in the Position &alpha to Polar Functional Groups. 1.2 C-H Transformation in the Allylic and Benzylic Positions. 1.3 C-H Transformation at Functionalized Alkanes via Palladacycles (Gerald Dyker). 2. C-H Transformation at Unfunctionalized Alkanes. 2.1 C-O Bond Formation by Oxidation. 2.2 Radical Halogenations of Alkanes (Peter R. Schreiner and Andrey A. Fokin). 2.3 Preparative SET C-H Transformations of Alkanes (Andrey A. Fokin and Peter R. Schreiner). 2.4 Photochemical Processes. 2.5 Heterogeneous Catalysts for the C-H Transformation of Unfunctionalized Alkanes (Robert Schlogl). 2.6 Transition-metal Catalyzed Carboxylation of Alkanes (Yuzo Fujiwara and Tsugio Kitamura). 2.7 Photochemical and Thermal Borylation of Alkanes (John F. Harwig and Joshua D. Lawrence). 2.8 Preparation of Olefins by Transition Metal-catalyzed Dehydrogenation (Alan S. Goldman and Rajshekhar Ghosh). 2.9 Rhodium-catalyzed Enantioselective Carbene Addition (Huw M.L. Davies). Index.