Palladium-catalyzed Heck-carbonylation of alkene-tethered carbamoyl chlorides with aryl formates

We report a palladium-catalyzed Heck-carbonylation of alkene-tethered carbamoyl chlorides by utilizing aryl formates as convenient CO surrogates. One C-O and two C-C bonds are constructed to give diversiform esterified oxindoles/& gamma;-lactams bearing an all-carbon quaternary stereocenter under gas-free conditions. This transformation features a wide substrate scope and good functional group tolerance and can be easily applied to late-stage functionalization.

Automated summary

We describe a palladium-catalyzed Heck-carbonylation reaction of alkene-tethered carbamoyl chlorides using aryl formates as convenient CO surrogates. This reaction allows for the construction of one C-O and two C-C bonds, resulting in the formation of diverse esterified oxindoles and γ-lactams with an all-carbon quaternary stereocenter under gas-free conditions. This transformation exhibits a broad substrate scope, excellent functional group tolerance, and can be readily applied for late-stage functionalization.