Loading…
Direct Transition-Metal-Free Intramolecular Arylation of Phenols
Direct transition-metal-free, base-mediated intramolecular arylation of phenols with aryl halides has been developed. In the presence of 2.5 equiv of t-BuOK in dioxane at 140 °C, the intramolecular cyclization of 3-(2-halobenzyloxy)phenols affords 6H-benzo[c]chromenes in high yields. This reaction p...
Saved in:
Published in: | Organic letters 2008-10, Vol.10 (20), p.4625-4628 |
---|---|
Main Authors: | , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
Summary: | Direct transition-metal-free, base-mediated intramolecular arylation of phenols with aryl halides has been developed. In the presence of 2.5 equiv of t-BuOK in dioxane at 140 °C, the intramolecular cyclization of 3-(2-halobenzyloxy)phenols affords 6H-benzo[c]chromenes in high yields. This reaction proceeds by an initial formation of a benzyne intermediate followed by an aromatic sp2 C−H functionalization (a formal C−H activation) to form the carbon−carbon bond. |
---|---|
ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/ol801897m |