4.2.8. Reductive Coupling 3109 5. Reaction of Aromatic Compounds 3110 5.1. Electrophilic Substitutions 3110 5.2. Radical Substitution 3111 5.3. Oxidative Coupling 3111 5.4. Photochemical Reactions 3111 6. Reaction of Carbonyl Compounds 3111 6.1. Nucleophilic Additions 3111 6.1.1. Allylation 3111 6.1.2. Propargylation 3120 6.1.3. Benzylation 3121 6.1.4. Arylation/Vinylation 3121 6.1.5. Alkynylation 3121 6.1.6. Alkylation 3121 6.1.7. Reformatsky-Type Reaction 3122 6.1.8. Direct Aldol Reaction 3122 6.1.9. Mukaiyama Aldol Reaction 3124 6.1.10. Hydrogen Cyanide Addition 3125 6.2. Pinacol Coupling 3126 6.3. Wittig Reactions 3126 7. Reaction of R,â-Unsaturated Carbonyl Compounds 3127

Organic Reactions in Aqueous Media with a Focus on Carbon−Carbon Bond Formations: A Decade Update

The notion of "green chemistry " has encouraged even synthetic organic chemists to include water as a solvent. Incredible selectivities and activities can be achieved through the addition of amphiphiles with a defined structure. The morphology of supramolecular assemblies or associates formed by surfactants vary according to the temperature and concentration. As a rule, reactions are typically conducted using simple spherical aggregates, that is, micelles in the nanometer range. The strong polarity gradient present between the hydrophilic surface and the hydrophobic core of the micelle means that both nonpolar and polar reagents can be solubilized. This solubilization results in reactants becoming more concentrated within the micelle than in the surrounding water phase and leads to an acceleration of the reaction and causes selective effects. The kinetic treatment of reactions in micellar systems can be accomplished by considering them as microheterogeneous two-phase systems.

Reactions in Micellar Systems

Recent progress in the synthesis of benzene and 1,3-cyclohexadiene derivatives, and heterocyclic compounds such as pyridines, pyridones, pyrans, pyrimidine diones, etc, has been reviewed. The general mechanistic aspects of the [2+2+2] cycloaddition reaction are discussed. The asymmetric variants of these reactions are also discussed along with the proposed models of asymmetric induction.

http://web4.uwindsor.ca/users/j/jlichaa/reference.nsf/0/10ff8b04ff3a317885256d88005720f6/$file/asc-2006-348-2307 2+2+2.pdf

[2+2+2] Cycloaddition Reactions Catalyzed by Transition Metal Complexes

http://www.uwindsor.ca/users/j/jlichaa/reference.nsf/0/10ff8b04ff3a317885256d88005720f6/$FILE/tet-2005-61-11771%20Heck%20non%20conv.pdf

Non-conventional methodologies for transition-metal catalysed carbon–carbon coupling: a critical overview. Part 2: The Suzuki reaction

Water is truly ubiquitous. Approximately 80% of the earth’s surface is covered by water, although only 1% of this is drinkable water. Water is the solvent of life and makes up about 60% of the mass of the human body. The majority of synthetic organic chemistry carried out in research laboratories or industrial processes utilizes organic solvents, however. Organic solvents have a number of attractive features: they will dissolve a wide range of organic compounds, they come with a variety of properties, and they are often volatile and easily removed. Unfortunately, organic solvents are often toxic, flammable, and nonrenewable and have low heat capacities. In contrast, water is nontoxic and nonflammable, has a high heat capacity, and is relatively inexpensive. Of course water has some significant drawbacks as a solvent: it is a poor solvent for most organic molecules, and it is highly reactive with many classes of reagents. Because of these drawbacks, water is rarely used as a primary solvent in synthetic organic chemistry, although there is a growing body of work related to organic chemistry in water.1-3

Hydrophilic Ligands and Their Application in Aqueous-Phase Metal-Catalyzed Reactions

Water Enables Direct Use of Allyl Alcohol for Tsuji−Trost Reaction without Activators

Macrocyclization via rhodium-catalyzed intramolecular [2 + 2 + 2] annulation of triynes has been explored in an aqueous−organic biphasic system. The biphasic system controls the concentration of hy...

Hidenori Kinoshita

Papers

Water Enables Direct Use of Allyl Alcohol for Tsuji−Trost Reaction without Activators

Rhodium-Catalyzed [2 + 2 + 2] Cyclotrimerization in an Aqueous−Organic Biphasic System

Hydrosilylation of alkynes with a cationic rhodium species formed in an anionic micellar system.

Phosphane-free rhodium catalyst in an anionic micellar system for [4+2] annulation of dienynes.

Biaryl synthesis from two different aryl halides with tri(2-furyl)germane.