Supporting Information Metal-mediated and Metal-catalyzed Reactions of Isocyanides

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1 Supporting Information Metal-mediated and Metal-catalyzed Reactions of Isocyanides Vadim P. Boyarskiy*, Nadezhda A. Bokach*, Konstantin V. Luzyanin*, Vadim Yu. Kukushkin* Institute of Chemistry, Saint Petersburg State University, Stary Petergof, Russian Federation 1

2 Supporting Information for Section 1. Introduction TABLE A1. Reviews and text-book considerations on organometallic chemistry of isocyanide species published up to the year Entry Publication year Author(s) Scope Refs 1969 L. Malatesta, F. Bonati Isocyanide Complexes of Metals (Book). Comprehensive work covering the preparation of free isocyanides, study of their properties and generation of their complexes with various metals. Chapter 1. Structure, properties and preparation of isocyanides. 112 refs. Chapter 2. General properties of isocyanide complexes. 66 refs. Chapter 3. Isocyanide complexes of main-group elements. 46 refs. Chapter 4. Isocyanide complexes of group VI elements. 37 refs. Chapter 5. Isocyanide complexes of group VII elements. 21 refs. Chapter 6. Isocyanide complexes of iron and ruthenium. 63 refs. Chapter 7. Isocyanide complexes of cobalt, rhodium and iridium. 45 refs. Chapter 8. Isocyanide complexes of nickel, palladium and platinum. 41 refs. Ref A. Vogler (in I. Ugi, Chemistry, Chapter 10) Chapter covering structure and bonding in metal isocyanide complexes, synthesis of metal isocyanide complexes, and reactions of coordinated isocyanides. 40 refs. Ref P. M. Treichel Preparation and reactivity of transition-metal isocyanide complexes towards wide range of reagents. 177 refs F. Bonati, G. Minghetti Structure and bonding in isocyanide complexes, reactions of coordinated isocyanides, synthesis of metal isocyanide complexes (recent advances: ). 238 refs. Ref. 3 Ref Y. Yamamoto Review covering zerovalent transition metal complexes of organic isocyanides. 172 refs. Ref E. Singleton, H. E. Oosthuizen Preparation of metal-isocyanide complexes, in particular, of chromium, molybdenum, and tungsten; electrochemical studies attempting to rationalize substituent effects on the isocyanide with the electronic structure of the metal; insertion reactions of isocyanides into metal alkyl or metal aryl bonds. Number of refs is not provided in Chemical Abstracts. Ref B. Crociani (in P.S. Braterman, Reactions of Coordinated Ligands) Tutorial review on reactions of complexed isocyanides. Number of refs is not provided in Chemical Abstracts. Ref. 7

3 1990 R. N. Vrtis, S. J. Lippard Reductive coupling of carbon monoxide and alkyl isocyanide ligands in early transition-metal complexes. 111 refs. Ref W. P. Fehlhammer, M. Fritz Comprehensive review covering coordination chemistry and reactivity of CN and CNH ligands at various metal Ref. 9 centers. 535 refs F. E. Hahn Coordination chemistry of multidentate isocyanide ligands and catalytic properties of their complexes were considered. 100 refs. Ref G. Lentz Review covering preparation and properties of the complexes with fluorinated isocyanides. 212 refs. Ref A. Dömling Isocyanide-based multicomponent reactions (IMCRs). 154 refs. Ref L. Weber Review covering synthesis of homoleptic metal isocyanide complexes. 23 refs. Ref M. Tamm, F. E. Hahn Reactions of ß-functionalized phenyl isocyanides. 123 refs. Ref. 14 References to Table 1 (1) Malatesta, L.; Bonati, F. Isocyanide Complexes of Metals; Wiley-Interscience Publication, (2) Vogler, A. In Isonitrile chemistry; Ugi, I., Ed.; Academic Press, Inc., (3) Treichel, P. M. Adv. Organometal. Chem. 1973, 11, 21. (4) Bonati, F.; Minghetti, G. Inorg. Chim. Acta 1974, 9, 95. (5) Yamamoto, Y. Coord Chem. Rev. 1980, 32, 193. (6) Singleton, E.; Oosthuizen, H. E. Adv. Organometal. Chem. 1983, 22, 209. (7) Crociani, B. In Reactions of Coordinated Ligands; Braterman, P. S., Ed.; Plenum Press, New York, (8) Vrtis, R. N.; Lippard, S. J. Israel J. Chem. 1990, 30,

4 (9) Fehlhammer, W. P.; Fritz, M. Chem. Rev. 1993, 93, (10) Hahn, F. E. Angew. Chem., Int. Ed. Engl. 1993, 32, 650. (11) Lentz, G. Angew. Chem., Int. Ed. Engl. 1994, 33, (12) Dömling, A. Combinatorial Chemistry & High Throughput Screening 1998, 1, 1. (13) Weber, L. Angew. Chem., Int. Ed. Engl. 1998, 37, (14) Tamm, M.; Hahn, F. E. Coord. Chem. Rev. 1999, 182,

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