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,Advanced Synthesis & Catalysis

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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
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2019-11-26 , DOI: 10.1002/adsc.201901175
Guoduan Liang _{1,

2,

3} , Yanjun Ji _{1,

3} , Hairui Liu _{1,

2,

3} , Yadong Pang _{1,

2,

3} , Bojun Zhou _{1,

2,

3} , Maosheng Cheng _{1,

3} , Yang Liu ₁ , Bin Lin _{1,

3} , Yongxiang Liu _{1,

2,

3}

Affiliation

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.

中文翻译：

底物与金属配体之间阳离子-π-π相互作用诱导的三氟甲磺酸银/ N-氟苯磺酰亚胺催化色胺-酰胺合成螺[吲哚啉-3,4'-哌啶]

N-氟苯磺酰亚胺（NFSI）是有机合成中最流行的氟化剂之一，被用作三氟甲磺酸银（AgOTf）的配体，以通过在底物和金属配体之间形成弱的非共价相互作用来协助捕获持久的螺二铝中间体。AgOTf / NFSI催化体系在色胺胺酰胺到螺[吲哚啉-3,4'-哌啶]衍生物的环异构化中得到了确认。通过各种合成底物和可商购的亲核试剂证明了底物的耐受性。基于实验观察和密度泛函理论（DFT）计算，提出了阳离子-π-π模型来阐明作用机理。

更新日期：2019-11-27

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