Palladium-catalyzed Heck/aminocarbonylation of alkene-tethered carbamoyl chlorides with nitro compounds for the synthesis of carbamoyl-substituted oxindoles

Abstract

A straightforward and efficient approach for the synthesis of carbamoyl-substituted oxindoles has been developed via a palladium-catalyzed Heck cyclization and reductive aminocarbonylation reaction of alkene-tethered carbamoyl chlorides with nitro compounds....

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

“…On the basis of our experimental observation and previous reports, 1,10–14 the most plausible palladium-catalyzed Heck carbonylation mechanism is depicted in Scheme 5. Initially, the acyl–Pd( ii ) species A generated via the oxidative addition between the Pd(0) complex and 1 undergoes intramolecular carbopalladation to form the alkyl–Pd( ii ) intermediate B .…”

“…11 In 2019, Zhang and co-workers described a palladium-catalyzed enantioselective intramolecular Heck-carbonylation of N -allyl benzamides by using aryl formates as the source of CO (Scheme 1f). 10 e Although palladium-catalyzed Heck-carbonylation reactions of alkene-tethered aryl halides have been extensively investigated in the past few years, Heck-carbonylation reactions of alkene-tethered carbamoyl chlorides 12 to access carbonylated oxindoles/γ-lactams have been significantly less studied. Recently, we realized a palladium-catalyzed Heck-carbonylation of alkene-tethered carbamoyl chlorides using Mo(CO) 6 as the carbonyl source (Scheme 1g).…”

Pd/NBE-Catalyzed One-Pot Modular Synthesis of Polycyclic Fused δ-Lactams and Investigation of Room-Temperature Phosphorescence

“…In recent decades, Tong, Chen, Lautens, Wang, our group, and others have collectively advanced a plethora of innovative synthetic transformations involving isolated carbamoyl chlorides. Furthermore, isolated carbamoyl chlorides have emerged as significant electrophiles for achieving ortho -carbamoylation in the Catellani reaction .…”