Pd‐Catalyzed Cascade Heck‐Type Annulation And Carbonylation to β‐Oxindolysulfoximidoyl Amides at Room Temperature

Abstract

An efficient intramolecular Heck annulation and trapping of the resulting cyclic α‐oxindolylpalladium species by CO (1 atm) and NH‐sulfoximine in a cascade protocol at room temperature was described, which offering 3,3‐disubstituted β‐indoly sulfoximidoyl amides in mostly excellent yields under very gentle reaction conditions.

Recent Advances in the Synthesis of Five‐membered Nitrogen Heterocycles Induced by Palladium Ions and Complexes

“…Chen et al developed the synthesis of 3,3-disubstituted βoxindolysulfoximidoyl amides. [126] They mixed acrylamides 26 e and NH-sulfoximines with Pd(OAc) 2 , PPh 3 , and DBU in toluene at room temperature and then treated the resulting solution under CO. Both iodo-and bromo-phenyl derivatives reacted efficiently with medium to excellent yields (Scheme 99).…”

Modular synthesis of 3,3-disubstituted oxindoles from nitrones and acrylic acids

“…Intramolecular annulation methods, including Heck-type coupling, [41][42][43][44][45][46][47][48][49][50] Friedel-Crafts reactions [51][52][53][54][55][56][57] and C(sp 2 )-H/C (sp 3 )-H coupling, [58][59][60] have emerged as alternative approaches (Scheme 1A, eqn (c) and (d)). These methods are efficient in forming 3,3-disubstituted oxindoles with highly functionalised benzenoid moieties.…”