1,2-Halogen Migration in Haloallenyl Ketones: Regiodivergent Synthesis of Halofurans
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- 12 July 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (30) , 10500-10501
- https://doi.org/10.1021/ja053290y
Abstract
Selective 1,2-iodine, bromine, and chlorine migration in haloallenyl ketones in the presence of Au catalyst has been demonstrated. It was found that, depending on the nature of the Au catalyst used, either selective bromine migration or hydrogen shift occurs, leading to the formation of 3- or 2-bromofurans, respectively. Halirenium intermediate was proposed for the unusual 1,2-halogen migration. This cascade transformation allows for mild and efficient synthesis of various types of 3-halofurans.Keywords
This publication has 25 references indexed in Scilit:
- The golden gate to catalysisOrganic & Biomolecular Chemistry, 2005
- Carene terpenoids by gold-catalyzed cycloisomerization reactionsChemical Communications, 2004
- AuCl3-Catalyzed Synthesis of Highly Substituted Furans from 2-(1-Alkynyl)-2-alken-1-onesJournal of the American Chemical Society, 2004
- Catalaytic Isomerization of 1,5-Enynes to Bicyclo[3.1.0]hexenesJournal of the American Chemical Society, 2004
- Synthesis of Phenanthrenes and Polycyclic Heteroarenes by Transition‐Metal Catalyzed Cycloisomerization ReactionsChemistry – A European Journal, 2004
- Platinum- and Gold-Catalyzed Cycloisomerization Reactions of Hydroxylated EnynesJournal of the American Chemical Society, 2004
- A Novel 1,2‐Migration of Acyloxy, Phosphatyloxy, and Sulfonyloxy Groups in Allenes: Efficient Synthesis of Tri‐ and Tetrasubstituted FuransAngewandte Chemie International Edition in English, 2004
- Convenient Synthetic Procedures for 2-Bromofuran and 2,5-DibromofuranSynthetic Communications, 1990
- A mild method for the synthesis of furans. Application to 2,5-bridged furano macrocyclic compoundsThe Journal of Organic Chemistry, 1990
- Base-catalyzed halogen dance, and other reactions of aryl halidesAccounts of Chemical Research, 1972