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Chiral sulfoxide is considered to be an ideal candidate ligand for transition-metal-catalyzed asymmetric reactions due to its ease of synthesis, stability, and exceptional S -stereological orientation control. This paper reviews the different types of asymmetrical reactions with chiral sulfoxide ligands in recent years, as well as a discussion of efficient methods for the preparation of some enantiomerically pure sulfoxides. 1 Introduction 2 Chiral Sulfoxides as Ligands in Metal-Catalyzed Asymmetric Catalysis 3 Synthesis of Chiral Sulfoxides 4 Conclusions [ABSTRACT FROM AUTHOR]

An odorless and efficient protocol for the synthesis of benzyl phenyl sulfides is reported. Starting from environmentally friendly phenyl dithiocarbamates and commercially available benzyl halides as starting materials, the target compounds (benzyl phenyl sulfides) could be obtained smoothly and easily by using copper salt as catalyst and Cs2 CO3 as base. This method features ligand/additive-free, the use of readily available starting materials, inexpensive catalysts, and good substrate suitability, illustrating its potentially synthetic value for the convenient preparation of some biologically active molecules. [ABSTRACT FROM AUTHOR]

A highly efficient method for the synthesis of S -aryl dithiocarbamates is reported. By using tetramethylthiuram monosulfide (TMTM) and aryl boronic acids as starting materials, C(sp2)–S bond-forming reactions proceed smoothly to give the desired aryl dithiocarbamates in good to excellent yields. The methodology features a simple procedure, broad functional group tolerance and excellent yields, whilst showing potential synthetic value for the preparation of a diverse range of biologically and pharmaceutically active compounds. [ABSTRACT FROM AUTHOR]

Organometallic compounds have become increasingly important in organic synthesis because of their high chemoselectivity and excellent reactivity. Recently, a variety of organometallic reagents were found to facilitate transition-metal-catalyzed cross-coupling reactions and nucleophilic addition reactions. Here, we have summarized the latest progress in cross-coupling reactions and in nucleophilic addition reactions with functionalized organometallic reagents present to illustrate their application value. Due to the tremendous contribution made by the Knochel group towards the development of novel organometallic reagents, this review draws extensively from their work in this area in recent years. Introduction 1 Transition-Metal-Catalyzed Cross Couplings Involving Organo-zinc Reagents 2 Transition-Metal-Catalyzed Cross Couplings Involving Organomagnesium Reagents 3 Transition-Metal-Free Cross Couplings Involving Zn and Mg -Organometallic Reagents 4 Nucleophilic Additions Involving Zn and Mg Organometallic Reagents 5 Cross-Coupling Reactions or Nucleophilic Additions Involving Mn, Al-, La-, Li-, Sm- and In-Organometallics 6 Conclusion [ABSTRACT FROM AUTHOR]

A new, efficient copper-catalyzed C(sp2)–S formation of phenyl dithiocarbamates starting from aryl iodides and tetramethylthiuram monosulfide (TMTM) was developed. The target compounds, phenyl dithiocarbamates with active sites, were synthesized smoothly in good to excellent yields. The easy performance, high yields, decent functional group compatibility, and cost-effective substrates make the protocol practical and attractive in C–S bond formation. [ABSTRACT FROM AUTHOR]

A highly efficient three-component protocol for the synthesis of the 2-alkylthiobenzoazoles is described. Tetramethylthiuram disulfide (TMTD) cyclized with o -aminothiophenols, generating the intermediate 2-mercaptobenzothiazoles, and the successive C–S coupling with halogenated alkanes afforded a series of 2-alkyl-substituted thiobenzothiazoles smoothly in a one-pot process. This procedure could also be utilized for the preparation of 2-alkyl-substituted thiobenzoxazoles and 2-alkyl-substituted thiobenzimidazoles. Inexpensive and easily available starting materials, metal catalyst-free, broad substrate scope, and water as solvent are the features of this protocol. [ABSTRACT FROM AUTHOR]

The efficient and enantioselective syntheses of arundinolides A and B have been accomplished for the first time from chiral pool methyl-2,3- O -isopropylidene-β- d -ribofuranoside and d -ethyl lactate. The key features of the total synthesis are intramolecular crotonyl migration and NaBH4-CuCl catalyzed regioselective reduction and cross-metathesis reaction. [ABSTRACT FROM AUTHOR]

An efficient and simple synthesis of 1-thiocarbamoylindoles is reported in which 1 H -indoles react with tetramethylthiuram monosulfide (TMTM) to give a series of 1-thiocarbamoylindoles that were obtained- in good to excellent yields. The procedure was promoted by Cs2 CO3 under transition-metal-free conditions and gives a simple entry to protected indoles. [ABSTRACT FROM AUTHOR]