Brønsted Acid Catalyzed Direct Annulation of Alkoxyallenes and Naphthols to Chroman Ketals-Reference-Cited by-同舟云学术

Brønsted Acid Catalyzed Direct Annulation of Alkoxyallenes and Naphthols to Chroman Ketals

Published:2022-02-14 Issue:09 Volume:54 Page:2148-2156
ISSN:0039-7881
Container-title:Synthesis
language:en
Short-container-title:Synthesis

Author:

Zhang Cong¹,Jiang Gaoxi²,He Maosheng²³,Zhang Jinlong²,Wang Hao-Yang⁴

Affiliation:

1. Institute of Advanced Materials, Key Laboratory of Flexible Electronics, Nanjing Tech University

2. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences

3. University of Chinese Academy of Sciences

4. Laboratory of Mass Spectrometry Analysis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences

Abstract

AbstractA straightforward Brønsted acid-catalyzed and scalable annulation of alkoxyallenes with simple naphthols was developed, affording chroman ketals in 49–84% yields. The versatile chroman ketals can be easily converted into coumarins by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated oxidation, and a series of 2-substituted chromans via nucleophilic substitutions.

Funder

National Natural Science Foundation of China

Natural Science Foundation of Jiangsu Province

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0040-1719892.pdf

Reference2 articles.

1. From Palladium to Brønsted Acid Catalysis: Highly Enantioselective Regiodivergent Addition of Alkoxyallenes to Pyrazolones

2. Natural and Synthetic Chromenes, Fused Chromenes, and Versatility of Dihydrobenzo[h]chromenes in Organic Synthesis