Nickel-Catalyzed Alkylation of Oxindoles with Secondary Alcohols

Abstract

Herein, we have demonstrated a simple nickelcatalyzed C-3-selective alkylation of 2-oxindoles using a wide variety of secondary alkyl alcohols. As a special highlight, functionalization of the cholesterol derivative was reported. Control experiments, initial mechanistic studies, and deuterium-labeling experiments were performed for the alkylation process.

Harnessing alcohols as sustainable reagents for late-stage functionalisation: synthesis of drugs and bio-inspired compounds

“…The late-stage functionalisation of cholesterol demonstrated the synthetic potential of the process (Scheme 11). 47…”

Room‐Temperature Synthesis of α‐Alkylated Indolin‐2‐ones via a Photo Assisted Iron Catalyzed Borrowing Hydrogen Reaction

“…[9] Later, the research group of Morrill and coworkers reported the iron-catalyzed C-alkylation of oxindoles at 150 °C. [10] Contributions from the groups of Gnanaprakasam, [11] Piersanti, [12] Sundararaju, [13] Banerjee, [14] Mitsudome, [15] Beller, [16] Balaraman [17] and Antonino [18] have illustrated that varieties of transition metals (Ru, Ir, Co, Ni, Mn, Ag…) were able to intrigue such alkylation reactions, leading to versatile alkylated oxindoles. Nevertheless, extremely high temperature was needed for these reactions.…”