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.

Palladium-catalyzed, ligand-free Suzuki reaction in water using aryl fluorosulfates.

The highly enantioselective construction of a quaternary carbon center of dihydroquinazoline by an asymmetric Mannich reaction and chiral recognition are described The key transformation was to establish the chiral trifluoromethyl quaternary carbon center by a diamine-Bronsted acid-catalyzed enantioselective and regioselective Mannich reaction of a methyl ketone and 4-trifluoromethyldihydroquinazoline An unusual phenomenon of self-discrimination of enantiomers in hydrogen-bonded dimers was observed A valuable intermediate was transformed into the enantiopure HIV reverse transcriptase inhibitor DPC 083 (>999 ee) simply by reduction of the carbonyl group and elimination of the hydroxy group in hexamethylphosphoric tramide (HMPA)

Highly Enantioselective Construction of a Quaternary Carbon Center of Dihydroquinazoline by Asymmetric Mannich Reaction and Chiral Recognition

Successive copper(I)-catalyzed cross-couplings in one pot: A novel and efficient starting point for synthesis of carbapenems

A Concise Formal Synthesis of (−)-Hamigeran B

A concise route toward the formal synthesis of (±)-cephalotaxine has been developed. An intermolecular Pauson–Khand reaction was adopted to construct the cyclopentenone ring efficiently with high regioselectivity.

Zuogang Huang

Papers

Palladium-catalyzed, ligand-free Suzuki reaction in water using aryl fluorosulfates.

Highly Enantioselective Construction of a Quaternary Carbon Center of Dihydroquinazoline by Asymmetric Mannich Reaction and Chiral Recognition

Successive copper(I)-catalyzed cross-couplings in one pot: A novel and efficient starting point for synthesis of carbapenems

A Concise Formal Synthesis of (−)-Hamigeran B

A Formal Synthesis of (±)-Cephalotaxine via Pauson–Khand Reaction