Transition-Metal-Catalyzed C−S, C−Se, and C−Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions

Department of Chemistry, Tianjin University, Tianjin 300072, China; Department of Applied Chemistry, China Agricultural University, Beijing 100193, China; UMR 6014 CNRS, Laboratoire COBRA de l’IRCOF, Université et INSA de Rouen, Rue Tesniere, F-76130 Mont Saint Aignan, France; and Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032, China

Asymmetric construction of stereogenic carbon centers featuring a trifluoromethyl group from prochiral trifluoromethylated substrates.

Catalytic Enantioselective Formation of C−C Bonds by Addition to Imines and Hydrazones: A Ten-Year Update

Sulfur-containing molecules such as thioethers are commonly found in chemical biology, organic synthesis, and materials chemistry. While many reliable methods have been developed for preparing these compounds, harsh reaction conditions are usually required in the traditional methods. The transition metals have been applied in this field, and the palladium-catalyzed coupling of thiols with aryl halides and pseudo halides is one of the most important methods in the synthesis of thioethers. Other metals have also been used for the same purpose. Here, we summarize recent efforts in metal-catalyzed C-S bond cross-coupling reactions, focusing especially on the coupling of thiols with aryl- and vinyl halides based on different metals.

Transition-metal-catalyzed C-S bond coupling reaction.

The Suzuki-Miyaura reaction (SMR), involving the coupling of an organoboron reagent and an organic halide or pseudo-halide in the presence of a palladium or nickel catalyst and a base, has arguably become one of most utilized tools for the construction of a C-C bond This review intends to be general account of all types of catalytic systems, new coupling partners and applications, including the literature between September 2010 and December 2014

Recent developments in the Suzuki-Miyaura reaction: 2010-2014.

Studies toward the total synthesis of nagelamide K.

A chemo- and stereoselective 1,4-hydrosilylation of alpha,beta-enone esters was developed using triethylsilane and trifluoroacetic acid under indium chloride catalysis.

A Mild Method for Indium(III)-Catalyzed 1,4-Hydrosilylation of α,β-Enone Esters with Triethylsilane and Trifluoroacetic Acid

Chiral P,O-ligands derived from N,O-phenylene prolinols for palladium-catalyzed asymmetric allylic alkylation

Co2(CO)8-mediated cycloisomerization of arylene 1,7-enynes

A procedure for the stereospecific synthesis of drospirenone has been developed. The key steps included the stereospecific reduction of the C7-tertiary alcohol with ZnI2/Et3SiH, a novel mild and stereospecific tertiary alcohol reduction system, and the tandem oxidation/cyclopropanation reactions.

Zuogang Huang

Papers

Studies toward the total synthesis of nagelamide K.

A Mild Method for Indium(III)-Catalyzed 1,4-Hydrosilylation of α,β-Enone Esters with Triethylsilane and Trifluoroacetic Acid

Chiral P,O-ligands derived from N,O-phenylene prolinols for palladium-catalyzed asymmetric allylic alkylation

Co2(CO)8-mediated cycloisomerization of arylene 1,7-enynes

Stereospecific Synthesis of Drospirenone