Palladium-Catalyzed Arylation/Heteroarylation of Indoles: Access to 2,3-Functionalized Indolines.

A palladium-catalyzed diastereoselective dearomatization of N-(2-bromobenzoyl)indoles by an arylation/heteroarylation sequence is reported. Diverse functionalized indolines are accessed in good to excellent yields and selectivity. Studies conducted on the effects of copper in the reaction revealed that, along with improving conversions, the additive inhibits epimerization of the product.

Palladium-Catalyzed Enantioselective Three-Component Synthesis of α-Arylglycines.

A general Pd-catalyzed, enantioselective three-component synthesis of α-arylglycines starting from sulfonamides, glyoxylic acid derivatives, and boronic acids was developed. This operationally straightforward procedure enables the preparation of a wide variety of α-arylglycines in high yields and excellent levels of enantioselectivity from a simple set of readily available starting materials. Incorporation of Pbf-amides gives a racemization-free access to N-unprotected α-arylglycines.

Palladium-Catalyzed Enantioselective Three-Component Synthesis of α-Substituted Amines.

The first general palladium-catalyzed, enantioselective three-component synthesis of α-arylamines starting from sulfonamides, aldehydes, and arylboronic acids has been developed. These reactions generate a wide array of α-arylamines with high yields and enantioselectivities. Notably, this process is tolerant to air and moisture, providing an operationally simple approach for the synthesis of chiral α-arylamines.

Bi(OTf)3-catalyzed three-component synthesis of α-amino acid derivatives.

A highly efficient Bi(OTf)3-catalyzed multicomponent synthesis of arylglycines from readily available starting materials is described. The reaction proceeds under mild conditions and provides a general route to various N-protected arylglycines.

A Lewis acid palladium(II)-catalyzed three-component synthesis of α-substituted amides.

A Lewis acid palladium-catalyzed reaction of amides, aryl aldehydes, and arylboronic acids is described. This new method allows for a practical and general synthesis of α-substituted amides from simple, readily available building blocks.