Silver Triflate/N‐Fluorobenzenesulfonimide‐Catalyzed Cycloisomerization of Tryptamine‐Ynamide to Spiro[indoline‐3, 4′‐piperidine] Induced by Cation‐π‐π Interactions between Substrate and Metal Ligand. Issue 1 (26th November 2019)

• Record Type: Journal Article
• Authors: Liang, Guoduan; Ji, Yanjun; Liu, Hairui; Pang, Yadong; Zhou, Bojun; Cheng, Maosheng; Liu, Yang; Lin, Bin; Liu, Yongxiang
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 1(2020)
• Page Start: 192
• Page End: 205
• Publication Date: 2019-11-26
• Subjects: Spiroindoline -- Ynesulfonamide -- Homogeneous catalysis -- Noncovalent interactions -- Cyclization -- Density functional theory calculation; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201901175
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: N ‐Fluorobenzenesulfonimide (NFSI), one of the most popular fluorinating agents in organic synthesis, was used as a ligand of silver triflate (AgOTf) to assist the trapping of the persistent spiroindoleninium intermediates by forming a weak noncovalent interaction between the substrate and metal ligand. The AgOTf/NFSI catalytic system was identified in the cycloisomerization of tryptamine‐ynamide to spiro[indoline‐3, 4′‐piperidine] derivatives. The substrate tolerances were demonstrated by various synthetic substrates and commercially available nucleophiles. A cation‐π‐π model was proposed to elucidate the mechanism of action based on the experimental observations and density functional theory (DFT) calculations. Abstract :