1.8 Metal-Catalyzed Intramolecular C—N and C—O Bond Formation
Book
Editors: Gao, S.; Ma, S.
Title: Metal-Catalyzed Cyclization Reactions 1
Print ISBN: 9783131998613; Online ISBN: 9783132403406; Book DOI: 10.1055/b-003-129294
1st edition © 2016 Georg Thieme Verlag KG
Georg Thieme Verlag, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry
Science of Synthesis Reference Libraries
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Koch, G.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.
Type: Multivolume Edition
Abstract

Transition-metal-catalyzed intramolecular C—N and C—O bond formation using unsaturated alkene and alkyne systems containing tethered nitrogen nucleophiles (such as amines, amides, sulfonamides, amidines, azides, carbamates, guanidines, hydrazones, imines, and ureas) or oxygen nucleophiles (such as alcohols, ketones, phenols, hydroxylamines, and carboxylic acids) represents an efficient method for the preparation of heterocycles. Various reaction types may be involved, including amination, hydroamination, oxidative amination, carbamoylation, carboamination, alkoxylation, hydroalkoxylation, oxidative alkoxylation, hydroacyloxylation, carboalkoxylation, and alkoxycarbonylation. Depending on the type of reaction, the choice of transition-metal complex to be used plays a fundamental role in obtaining a successful reaction.
Key words
alkoxycarbonylation - alkoxylation - amination - carbamoylation - carboalkoxylation - carboamination - hydroacyloxylation - hydroalkoxylation - hydroamination - intramolecular C—N bond formation - intramolecular C—O bond formation - oxidative amination - oxidative alkoxylation - transition-metal catalysis- 12 Krause N, Aksin-Artok Ö, Breker V, Deutsch C, Gockel B, Poonoth M, Sawama Y, Sawama Y, Sun T, Winter C. Pure Appl. Chem. 2010; 82: 1529
- 16 Müller TE, Grosche M, Herdtweck E, Pleier A.-K, Walter E, Yan Y.-K. Organometallics 2000; 19: 170
- 33 Zulys A, Dochnahl M, Hollmann D, Löhnwitz K, Herrmann J.-S, Roesky PW, Blechert S. Angew. Chem. Int. Ed. 2005; 44: 7794
- 51 Broggini G, Barbera V, Beccalli EM, Chiacchio U, Fasana A, Galli S, Gazzola S. Adv. Synth. Catal. 2013; 355: 1640
- 90 Orito K, Horibata A, Nakamura T, Ushito H, Nagasaki H, Yuguchi M, Yamashita S, Tokuda M. J. Am. Chem. Soc. 2004; 126: 14342
- 111 Takahashi M, Tanabe H, Nakamura T, Kuribara D, Yamazaki T, Kitagawa O. Tetrahedron 2010; 66: 288
- 113 Schwartz RE, Liesch J, Hensens O, Zitano L, Honeycutt S, Garrity G, Fromtling RA, Onishi J, Monaghan R. J. Antibiot. 1988; 41: 1774
- 114 Kinzy TG, Harger JW, Carr-Schmid A, Kwon J, Shastry M, Justice M, Dinman JD. Virology 2002; 300: 60
- 132 Genin E, Toullec PY, Antoniotti S, Brancour C, Genêt J.-P, Michelet V. J. Am. Chem. Soc. 2006; 128: 3112
- 139 Smith III AB, Guaciaro MA, Schow SR, Wovkulich PM, Toder BH, Hall TW. J. Am. Chem. Soc. 1981; 103: 219
- 155 Larock RC, Yang H, Pace P, Narayanan K, Russell CE, Cacchi S, Fabrizi G. Tetrahedron 1998; 54: 7343