Premium
PdCl 2 /CuCl 2 /Bi(OTf) 3 ‐promoted Construction of Sulfonyl Dibenzooxabicyclo[3.3.1]nonanes and Arylnaphthalenes via Intramolecular Annulation of Sulfonyl o ‐Allylarylchromanones
Author(s) -
Hsueh NaiChen,
Chang MengYang
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001021
Subject(s) - annulation , sulfonyl , chemistry , intramolecular force , ring (chemistry) , catalysis , intermolecular force , medicinal chemistry , stereochemistry , organic chemistry , molecule , alkyl
PdCl 2 /CuCl 2 /Bi(OTf) 3 ‐promoted intramolecular domino annulation of sulfonyl o ‐allylarylchromanones provides tetracyclic sulfonyl dibenzooxabicyclo[3.3.1]nonanes and bicyclic arylnaphthalenes with good to excellent yields in MeOH at room (25 °C) and refluxing (65 °C) temperature, respectively. The starting sulfonyl o ‐allylarylchromanones can be easily obtained from the intermolecular cyclocondensation of α‐sulfonyl o ‐hydroxyacetophenones and o ‐allylbenzaldehydes. The uses of various catalysts and solvent systems are investigated herein for convenient transformation. A plausible mechanism is proposed and discussed. This protocol provides one‐pot ring closure via carbon‐carbon (C−C) bond formation.