Access to Functionalized Indenes via Palladium‐Catalyzed Homolytic Cleavage of a Furan C−O Bond-Reference-Cited by-同舟云学术

Access to Functionalized Indenes via Palladium‐Catalyzed Homolytic Cleavage of a Furan C−O Bond

Published:2024-08-06 Issue: Volume: Page:
ISSN:1615-4150
Container-title:Advanced Synthesis & Catalysis
language:en
Short-container-title:Adv Synth Catal

Author:

Jiang Kai¹,Zeng Guohui¹,Xie Xinyue¹,Luo Hui²,Fan Qi¹,Yin Biaolin¹^ORCID

Affiliation:

1. Key Laboratory of Functional Molecular Engineering of Guangdong Province School of Chemistry and Chemical Engineering South China University of Technology (SCUT) Guangzhou 510640 People's Republic of China

2. Guangzhou Addenda Chemical Corp. Ltd, Huangpu Guangzhou 510663 People's Republic of China

Abstract

AbstractA photoinduced palladium‐catalyzed ring‐opening hydroarylation of furans to form functionalized indenes was achieved via an intramolecular reductive coupling of aryl bromide with furan using silane as the reductant. Deuterium tracking and DFT analysis revealed a reasonable reaction pathway involving: 1) the homolytic cleavage of the furan C−O bond induced by the α‐allyl radical; 2) a 1,6‐H atom transfer from carbon to oxygen.

Funder

Natural Science Foundation of Guangdong Province

Publisher

Wiley

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.202400297

Reference71 articles.

1. For selected examples see:

2. Copper-Catalyzed Addition of Ethyl Diazoacetate to Furans: An Alternative to Dirhodium(II) Tetraacetate

3. Gold-Catalyzed Approach to Multisubstituted Fulvenes via Cycloisomerization of Furan/Ynes

4. Furfuryl Cation Induced Cascade Formal [3 + 2] Cycloaddition/Double Ring-Opening/Chlorination: An Approach to Chlorine-Containing Complex Triazoles

5. Synthesis of Penta-2,4-dien-1-imines and 1,2-Dihydropyridines by Rhodium-Catalyzed Reaction of N-Sulfonyl-1,2,3-triazoles with 2-(Siloxy)furans