Dapeng Zou

The palladium-catalyzed cross-coupling reactions of trifluoroethyl iodide with aryl and heteroaryl boronic acid esters

The cross-coupling reactions of 1,1,1-trifluoro-2-iodoethane with aryl and heteroaryl boronic acid esters have been successfully achieved. The new protocol allows for a convenient introduction of trifluoroethyl groups into a variety of aryl and heteroaryl moieties under mild conditions.

Facile synthesis of trifluoroethyl compounds by the Suzuki cross-coupling reactions of CF3CH2OTs with arylboronic acids

This research provides a novel approach for introducing a CF3CH2 group onto aromatic rings using Pd(OAc)2/palladacycle as a catalyst for the Suzuki cross-coupling reaction of CF3CH2OTs (OTs = 4-methylbenzene sulfonate) with arylboronic acids.

Regioselective Synthesis of N-Heteroaromatic Trifluoromethoxy Compounds by Direct O-CF3 Bond Formation.

The first one-step method for the synthesis of ortho-N-heteroaromatic trifluoromethoxy derivatives by site-specific O-CF3 bond formation using hydroxylated N-heterocycles and Tognis reagent is described. The approach enables the unprecedented syntheses of a wide range of six or five-membered N-heteroaromatic trifluoromethoxy compounds containing one or two heteroatoms from most commonly used hydroxylated N-heterocycles. Notable advantages of this method include its simplicity and mild conditions, avoidance of the need for metals or toxic reagents, and compatibility with a variety of functional groups. Furthermore, this method is especially suitable for the larger scale application.

Metal-Free Reduction of Aromatic Nitro Compounds to Aromatic Amines with B2pin2 in Isopropanol

A metal-free reduction of aromatic nitro compounds to the corresponding amines has been achieved by a combination of B2pin2 and KOtBu in isopropanol. A series of nitro compounds containing various reducible functional groups were chemoselectively reduced in good to excellent yields.

Preparation of tert-Butyl Esters via Pd-Catalyzed tert-Butoxycarbonylation of (Hetero)aryl Boronic Acid Derivatives

A novel protocol to synthesize tert-butyl esters from boronic acids or boronic acid pinacol esters and di-t-butyl dicarbonate has been successfully achieved. The cross-coupling reactions can produce up to 94% yields by using palladium acetate and triphenylphosphine as catalyst system, dioxane as a solvent. Moreover, a wide range of substrates including benzenes, pyridines, and quinolines boronic acids or boronic acid pinacol esters can fit with this system as well.

Pd-Catalyzed Tandem Cyclization via C–H Arylation and Acylation for the Construction of Polycyclic Scaffolds

The first Pd-catalyzed tandem cyclization of imidazo[1,2-a]pyridines with 2-chlorobenzaldehydes through C-H arylation and acylation is presented for the efficient synthesis of novel 6H-benzo[b]imidazo[5,1,2-de]quinolizin-6-ones. The direct acylation reaction proceeded smoothly without the aid of directing groups and in the presence of air as a clean and free terminal oxidant.

Palladium-Catalyzed Diastereoselective Synthesis of 3-Arylbutanoic Acid Derivatives

The first palladium-catalyzed diastereoselective conjugate addition of arylboronic acids to chiral imides is reported. The catalytic system employing 4-tert-butyloxazolidin-2-one as the chiral auxiliary in a mixed solvent system of MeOH/H2O (1:3) under an air atmosphere provides the optically active 3-arylbutanoic acid derivatives in excellent yields with high diastereoselectivity.

Stereoselective synthesis of 2,2-bis(C-branched-chain)glucopyranosid-3-ulose via an autoxidation?Michael addition reactionElectronic supplementary information (ESI) available: spectroscopic data for 2?7. See http://www.rsc.org/suppdata/cc/b3/b306227a/

2,2-Bis(C-branched-chain)glucopyranosid-3-uloses, designed for the preparation of biologically active natural product iridoid derivatives, are synthesized selectively by the new reaction of butenolide-containing sugar with active methylene compounds, and the new reaction is clarified as autoxidation followed by Michael addition of carbanion.

CuI-Catalyzed Fluorodesulfurization for the Synthesis of Monofluoromethyl Aryl Ethers

An efficient CuI-catalyzed fluorodesulfurization for the synthesis of monofluoromethyl aryl ethers using DAST at room temperature has been developed. This approach exhibits a good functional group tolerance, a broad substrate scope, and a high synthesis efficiency.

Pd-Catalyzed Alkylation of (Iso)quinolines and Arenes: 2-Acylpyridine Compounds as Alkylation Reagents

The first Pd-catalyzed alkylation of (iso)quinolines and arenes is reported. The readily available and bench-stable 2-acylpyridine compounds were used as an alkylation reagent to form the structurally versatile alkylated (iso)quinolines and arenes. The method affords a convenient pathway for the introduction of alkyl groups into organic molecules.