Oxalyl amide assisted palladium-catalyzed synthesis of pyrrolidones via carbonylation of γ-C(sp3)–H bonds of aliphatic amine substrates

Oxalyl amide assisted palladium-catalyzed synthesis of pyrrolidones via carbonylation of γ-C(sp3)–H bonds of aliphatic amine substrates† †Electronic supplementary information (ESI) available: Experimental procedures, characterization data for all new compounds. CCDC 1048649. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc00519a

Ligand-assisted palladium-catalyzed C–H alkenylation of aliphatic amines for the synthesis of functionalized pyrrolidines

The development of a ligand-assisted Pd-catalyzed C–H alkenylation of aliphatic amines is reported. Our studies indicated that an amino-acid-derived ligand renders the C–H bond activation step reversible and promotes the traditionally difficult alkenylation process. The C(sp)–H alkenylation proceeds through a 5-membered-ring cyclopalladation pathway that allows access to complex aliphatic heter...

Facile synthesis of 12-carboxamido-11-spirostenes via palladium-catalyzed carbonylation reactions.

12-Carboxamido- and 12-carboxyl-11-spirostenes were synthesized from the corresponding 12-iodo-11-ene derivative in palladium-catalyzed carbonylation reactions under mild reaction conditions. The synthesis of the iodo-alkene substrate is based on the transformation of the 12-keto derivative (hecogenin) to hydrazone, which was treated with iodine in the presence of a base (1,1,3,3-tetramethyl gu...

Nickel-catalyzed transamidation of aliphatic amide derivatives.

Transamidation, or the conversion of one amide to another, is a long-standing challenge in organic synthesis. Although notable progress has been made in the transamidation of primary amides, the transamidation of secondary amides has remained underdeveloped, especially when considering aliphatic substrates. Herein, we report a two-step approach to achieve the transamidation of secondary aliphat...

Palladium-catalyzed regioselective carbonylation of C-H bonds of N-alkyl anilines for synthesis of isatoic anhydrides.

A Pd-catalyzed regioselective C-H bond carbonylation of N-alkyl anilines for the synthesis of isatoic anhydrides has been developed. The key Pd-catalyst intermediate has been isolated and characterized. This novel Pd-catalyzed carbonylation reaction tolerates a wide range of functional groups and is a reliable method for the rapid elaboration of readily available N-alkyl anilines into a variety...