8.4.5. Nitromercuration Reactions 3878 9. Hydroamination of Alkenes and Alkynes under Microwave Irradiation 3878 * To whom correspondence should be addressed. Phone: +49 241 8

Hydroamination: direct addition of amines to alkenes and alkynes.

3.15. Miscellaneous Photophysical Studies 1874 3.16. Dendritic Fluorescent Sensors 1875 3.17. Nonlinear Optical Properties 1875 4. Supramolecular Properties 1876 4.1. Concepts and Pioneering Studies 1876 4.2. H-Bonding 1877 4.3. Electrostatic Binding 1877 4.4. Combined H-Bonding/Ionic Bonding 1879 4.5. Coordination of Metal Ions 1880 4.6. Intradendritic π-π Interactions 1880 4.7. Encapsulation of Neutral Guest Molecules 1881 4.8. Interdendritic Supramolecular Associations 1883 4.8.1. Liquid Crystals 1883 4.8.2. Other Dendritic Self-Assemblies 1884 4.9. Supramolecular Assemblies between Dendrimers and Surfactants or Polymers 1885

Dendrimers Designed for Functions: From Physical, Photophysical, and Supramolecular Properties to Applications in Sensing, Catalysis, Molecular Electronics, Photonics, and Nanomedicine

Fluorine has received great attention in all fields of science. “Small atom with a big ego” was the title of the Symposium at the ACS meeting in San Francisco in 2000, where a number of the current scientific and industrial aspects of fluorine chemistry made possible by the small size and high electronegativity of the atom were discussed. This small atom has provided mankind with significant benefits in special products such as poly(tetrafluroethylene) (PTFE), freon, fluoro-liquid crystals, optical fiber, pharmaceutical and agrochemical compounds, and so on, all of which have their own unique properties that are otherwise difficult to obtain.1 For instance, at present, up to 30% of agrochemicals and 10% of pharmaceuticals currently used contain fluorine atoms. Therefore, organic fluorine compounds have received a great deal of interest and attention from the scientists involved in diverse fields of science and technology. Now, not only C-F bond formation but also selective C-F bond activation have become current subjects of active investigation from the viewpoint of effective synthesis of fluoroorganic compounds. The former is highlighted by designing a sophisticated fluorinating reagent for regioand stereocontrolled fluorination and developing versatile multifunctional and easily prepared building blocks. C-F bond formation has been treated extensively in several reviews2 and books.3 The latter is a subject that has been less explored but would be promising for selective defluorination of aliphatic fluorides, cross-coupling with aryl fluorides, and * To whom correspondence should be addressed. Phone: 81-78-803-5799. Fax: 81-78-803-5799. E-mail: amii@kobe-u.ac.jp and uneyamak@cc.okayamau.ac.jp. † Kobe University. ‡ Okayama University. Chem. Rev. 2009, 109, 2119–2183 2119

C-F bond activation in organic synthesis.

Organolanthanides are highly efficient catalysts for inter- and intramolecular hydroamination of various C−C unsaturations such as alkenes, alkynes, allenes, and dienes. Attractive features of organolanthanide catalysts include very high turnover frequencies and excellent stereoselectivities, rendering this methodology applicable to concise synthesis of naturally occurring alkaloids and other polycyclic azacycles. The general hydroamination mechanism involves turnover-limiting C−C multiple bond insertion into the Ln−N bond, followed by rapid protonolysis by other amine substrates. Sterically less encumbered ligand designs have been developed to improve reaction rates, and metallocene and nonmetallocene chiral lanthanide complexes have been synthesized for enantioselective hydroamination.

Organolanthanide-catalyzed hydroamination.

Late transition metal-catalyzed hydroamination and hydroamidation.

A simple colorimetric assay of various transition-metal catalysts showed that the combination of DPPF, Ni(COD)(2), and acid is a highly active catalyst system for the hydroamination of dienes by alkylamines to form allylic amines. The scope of the reaction is broad; various primary and secondary alkylamines react with 1,3-dienes in the presence of these catalysts. Detailed mechanistic studies revealed the individual steps involved in the catalytic process. These studies uncovered unexpected thermodynamics for the addition of amines to pi-allyl nickel complexes: instead of the thermodynamics favoring the reaction of a nickel allyl with an amine to form an allylic amine, the thermodynamics favored reaction of a nickel(0) complex with allylic amine in the presence of acid to form a Ni(II) allyl. The realization of these thermodynamics led us to the discovery that nickel and some palladium complexes in the presence or absence of acid catalyze the exchange of the amino groups of allylic amines with free amines. This exchange process was used to reveal the relative thermodynamic stabilities of various allylic amines. In addition, this exchange reaction leads to racemization of allylic amines. Therefore, the relative rate for C-N bond formation and cleavage influences the enantioselectivity of diene hydroaminations.

A general nickel-catalyzed hydroamination of 1,3-dienes by alkylamines: catalyst selection, scope, and mechanism.

A One-Pot Access to 6-Substituted Phenanthridines from Fluoroarenes and Nitriles via 1,2-Arynes

Novel Anionic Anellation Tactics for Construction of Fused Heteroaromatic Frameworks. Part 1. Synthesis of 4‐Substituted Pyrazolo[4,3‐c]quinolines, 9‐Substituted Pyrazolo[3,4‐c]quinolines, and 1,4‐Dihydrochromeno[4,3‐c]pyrazoles.

Environmentally Sensible Organocatalytic Fmoc/t-Bu Solid-Phase Peptide Synthesis.

Selective C* halogenation (I and Br) of pyrazoles 1a, 3a and 4a gave halopyrazoles 5, 7–9, 11, 12. Reactivity differences between 1a, 3a and 4a, and the failure of 2a to give the expected halopyrazoles 6, 10 were explained using calculated relative energies of bromination, and inspection of frontier molecular orbitals. Utility of the prepared halides was demonstrated by a series of palladium-catalysed cross-coupling reactions.

Halogenation of pyrazoloquinolines and pyrazoloisoquinolines. Theoretical analysis of the regioreactivity and cross-coupling of 3-halogen derivatives

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