Silyl-Triflate-Catalyzed Divergent Annulation of Isoquinolines with Ynamides: Direct Access to 2-Aminonaphthalenes and 2-Amino-1-naphthonitriles

Organic Letters 2026

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Authors: Longyu Xiao, Shuai Feng, Yu Yan, Xiaona Wang
DOI: 10.1021/acs.orglett.6c01317
Cited by: 1
References: 40

Abstract

Metal-free, silyl-triflate-catalyzed formal inverse-electron-demand Diels-Alder annulation of isoquinolines with ynamides enables the divergent synthesis of 2-aminonaphthalenes and 2-amino-1-naphthonitriles. The 3-substituent on isoquinoline dictates product selectivity: H or Me leads to nitrile extrusion, whereas Cl or Br triggers HX elimination. The transformation features a broad substrate scope, good scalability, and unified catalytic cycle involving substituent-directed bifurcation from a common bicyclic imine intermediate. This work offers a practical, metal-free route to functionalized naphthalenes and new insights into Lewis-acid-catalyzed annulations.

Fields of Study & Subjects

Catalytic Alkyne Reactions Catalytic C–H Functionalization Methods Cyclization and Aryne Chemistry

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
18
Pages
5804–5809
Publication date
25 April 2026
Language
EN