Chen-Liang Deng

Synthesis of (2-Oxoindolin-3-ylidene)methyl Acetates Involving a C−H Functionalization Process

A novel palladium-catalyzed oxidative C-H functionalization protocol for the synthesis of (2-oxoindolin-3-ylidene)methyl acetates has been developed. In the presence of Pd(OAc)2 and PhI(OAc)2, a variety of N-arylpropiolamides underwent the C-H functionalization reaction with acids to afford the corresponding (E)-(2-oxoindolin-3-ylidene)methyl acetates selectively in moderate to excellent yields.

Palladium-Catalyzed Oxidative Coupling of Trialkylamines with Aryl Iodides Leading to Alkyl Aryl Ketones

A new, simple method for selectively synthesizing alkyl aryl ketones has been developed by palladium-catalyzed oxidative coupling of trialkylamines with aryl iodides. In the presence of PdCl(2)(MeCN)(2), TBAB, and ZnO, a variety of aryl iodides underwent an oxidative coupling reaction with tertiary amines and water to afford the corresponding alkyl aryl ketones in moderate to excellent yields. It is noteworthy that this method is the first example of using trialkylamines as the carbonyl sources for constructing alkyl aryl ketone skeletons.

Copper/Silver-Cocatalyzed Conia−Ene Reactions of 2-Alkynic 1,3-Dicarbonyl Compounds

A copper/silver-catalyzed Conia-ene reaction has been developed for selectively constructing five-membered and six-membered rings. In the presence of (CuOTf)(2) x C(6)H(6) and AgBF(4), a variety of 2-alkynic 1,3-dicarbonyl compounds underwent the Conia-ene intramolecular reaction smoothly in moderate to good yields. It is noteworthy that both 2-phenylacetylhept-6-ynenitrile and diethyl 2-(pent-4-ynyl)malonate are also suitable substrates under the standard conditions, and the selectivity toward endo- or exo-products depends on the substituents at the terminal of alkynes.

Synthesis of 6-(trifluoromethyl)phenanthridines via palladium-catalyzed tandem Suzuki/C-H arylation reactions.

A palladium-catalyzed tandem Suzuki/C-H arylation reaction of N-aryltrifluoroacetimidoyl chlorides with arylboronic acids has been developed. A variety of 6-(trifluoromethyl)phenanthridines were prepared in moderate to excellent yields from N-(2-bromophenyl)trifluoroacetimidoyl chlorides which can be conveniently prepared from 2-bromoaniline derivatives.

Palladium and Copper Cocatalyzed Tandem N–H/C–H Bond Functionalization: Synthesis of CF3-Containing Indolo- and Pyrrolo[2,1-a]isoquinolines

A palladium- and copper-catalyzed tandem N-H/C-H bond functionalization reaction of ortho-(2-chlorovinyl)bromobenzenes with indoles and pyrroles has been developed. A variety of CF(3)-containing indolo- and pyrrolo[2,1-a]isoquinolines were prepared in moderate to good yields via the cyclization of 1-bromo-2-(2-chloro-3,3,3-trifluoroprop-1-enyl)benzenes with indoles and pyrroles.