F-DIAD is the fluorous equivalent of DIAD or DEAD and can be used in Mitsunobu reactions in conjunction with an appropriate phosphine. The phosphine can be traditional triphenylphosphine, a fluorous phosphine, or even a solid supported phosphine. When used together with the appropriate fluorous phosphine, a single fluorous separation, either F-SPE or liquid-liquid extraction, can effect separation of both the phosphine oxide and the hydrazine byproducts. A range of acidic nucleophiles including carboxylic acids, phenols, and phthalimides can be used. In addition the F-DIAD is thermally more stable than DIAD or DEAD.
- Hughes, D. L. Progress in the Mitsunobu reaction. A review. Org. Prep. Proced. Int. 1996, 28, 127-164. Hughes, D. L. The Mitsunobu reaction. Org. React. 1992, 42, 335-656. Dandapani, S.; Curran, D. P. Separation-friendly Mitsunobu reactions: A microcosm of recent developments in separation strategies. Chem. Eur. J. 2004, 10, 3130-3138.
- Dandapani, S.; Curran, D. P. Second generation fluorous DEAD reagents have expanded scope in the Mitsunobu reaction and retain convenient separation features. J. Org. Chem. 2004, 69, 8751-8757.
- Curran, D. P.; Bajpai, R.; Sanger, E. “Purification of fluorous Mitsunobu reactions by liquid-liquid extraction” Adv. Synth. Catal. 2006, 348, 1621 – 1624.
- Dembinski, R., "Approaches to the fluorous Mitsunobu reaction. "Handbook of Fluorous Chemistry" 2004, 190-202.
Examples utilizing a fluorous Mitsunobu:
- Jagadeshwar Vannada, Eric M. Bennett, Daniel J. Wilson, Helena I. Boshoff, Clifton E. Barry, III, and Courtney C. Aldrich “Design, Synthesis, and Biological Evaluation of beta-Ketosulfonamide Adenylation Inhibitors as Potential Antitubercular Agents” Org. Lett. 2006, 8, 4707-4710.
- Bimbisar Desai, Doris Dallinger and C. Oliver Kappe “Microwave-assisted solution phase synthesis of dihydropyrimidine C5 amides and esters” Tetrahedron 2006, 62, 4651-4664.
- Pierre-Yves Dakas, Sofia Barluenga, Frank Totzke, Ute Zirrgiebel, Nicolas Winssinger “Modular Synthesis of Radicicol A and Related Resorcylic Acid Lactones, Potent Kinase Inhibitors” Angewandte Chemie International Edition 2007, 46, 6899-6902.
- Gerard, B.; Cencic, R.; Pelletier, J.; Porco, J.A. Jr., Enantioselective Synthesis of the Complex Rocaglate (-)-Silvestrol, Angew. Chem. Intl. Ed. 2007, DOI: 10.1002/ange.200702707