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PdCl2/CuCl2/Bi(OTf)3‐promoted Construction of Sulfonyl Dibenzooxabicyclo[3.3.1]nonanes and Arylnaphthalenes via Intramolecular Annulation of Sulfonyl o‐Allylarylchromanones
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-11-02 , DOI: 10.1002/adsc.202001021
Nai‐Chen Hsueh, Meng‐Yang Chang

PdCl2/CuCl2/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.

中文翻译:

PdCl2 / CuCl2 / Bi(OTf)3促进的磺酰基邻烯丙基芳基苯并二氢呋喃酮的分子内环化反应构建磺酰基二苯并恶双环[3.3.1]壬烷和芳基萘

PdCl 2 / CuCl 2 / Bi(OTf)3促进的磺酰基烯丙基芳基苯并二氢呋喃酮分子内环化反应提供了四环磺酰基二苯并氧杂双环[3.3.1]壬烷和双环芳基萘,在室温(25°C)和回流条件下,在MeOH中的产率高至优异(65°C)温度。起始磺酰ø -allylarylchromanones可以从α磺酰基的分子间环化缩合而容易地获得ö -hydroxyacetophenones和ö烯丙基甲醛。为了方便的转化,本文研究了各种催化剂和溶剂体系的用途。提出并讨论了一种可行的机制。该协议通过碳-碳(CC)键的形成提供一锅闭环。
更新日期:2020-12-23
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