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.

The intermolecular Pauson-Khand reaction between 2-ethynylbenzaldehyde and ethylene promoted by dimethyl sulfide can be utilized to synthesize 2-(2-formylphenyl)cyclopentenone efficiently. This compound and its derivatives undergo a cascade process of Michael addition reaction followed by Henry reaction with nitromethane to construct substituted aromatic fused 2,3-dihydroindanones. Furthermore, direct one-pot synthesis of aromatic fused 2,3-dihydroindanones from 2-ethynylbenzaldehyde is achieved.

One-pot Synthesis of Aromatic Fused 2,3-Dihydroindanone by Tandem Pauson-Khand/Michael/Henry Reaction

Easily prepared aryl fluorosulfates are used as coupling partners in the Suzuki—Miyaura reaction.

Palladium‐Catalyzed, Ligand‐Free Suzuki Reaction in Water Using Aryl Fluorosulfates.

In the presence of Co2(CO)8 and additives, propargyl alcohol derivatives could be reduced to alkenes in moderate to good yield. The selectivity of this reaction could be controlled by adding different additives: with H2O as the additive, the major configuration of product is Z-alkene; with CF3COOH as the additive, the major configuration of product is E-alkene.

Co2(CO)8-mediated Selective Reductions of Propargyl Alcohol Derivatives to Alkenes

Spiroborate-based dimeric assembly of oligo(ethylene glycol) end-capped with phenolic gallates

α-Keto esters of type (I) undergo an efficient stereoselective hydrosilylation give moderate yields of the desired α,β-unsaturated esters (III).

Zuogang Huang

Papers

One-pot Synthesis of Aromatic Fused 2,3-Dihydroindanone by Tandem Pauson-Khand/Michael/Henry Reaction

Palladium‐Catalyzed, Ligand‐Free Suzuki Reaction in Water Using Aryl Fluorosulfates.

Co2(CO)8-mediated Selective Reductions of Propargyl Alcohol Derivatives to Alkenes

Spiroborate-based dimeric assembly of oligo(ethylene glycol) end-capped with phenolic gallates

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