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Pd-Catalyzed Synthesis of Dibenzofurans by Phenol-Directed C-H Activation
| Content Provider | Scilit |
|---|---|
| Copyright Year | 2011 |
| Description | Reported is the synthesis of dibenzofurans 2 from 2-arylphenols 1 via palladium-catalyzed phenol-directed C-H activation/C-O cyclization. Control experiments (formation of stoichiometric Pd complexes and isotope labeling studies) showed that C-O reductive elimination was the rate-limiting step. Accordingly, the bulky additive $MesCO_{2}$Na was found to increase the yield by promoting reductive elimination. A broad range of functionalities (including acid-sensitive groups, heterocycles, and even sugars) are tolerated, many of which provide synthetic handles for further functionalization. To demonstrate the orthogonality of this method with an established related carbazole synthesis (J. A. Jordan-Hore, C. C. C. Johansson, M. Gulias, E. M. Beck, M. J. Gaunt J. Am. Chem. Soc. 2008, 130, 16184), compound 3 was prepared by selective C-O coupling to form the dibenzofuran followed by C-N coupling to afford the carbazole. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0030-1261002.pdf |
| Ending Page | 0941 |
| Page Count | 1 |
| Starting Page | 0941 |
| ISSN | 18611958 |
| e-ISSN | 1861194X |
| DOI | 10.1055/s-0030-1261002 |
| Journal | Synfacts |
| Issue Number | 09 |
| Volume Number | 2011 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2011-08-19 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synfacts Organic Chemistry Functionalization |
| Content Type | Text |
| Resource Type | Article |
