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Fluorous Mitsunobu reagents and reactions

Sivaraman Dandapani and Dennis P. Curran*

*Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA, Email:

S. Dandapani, D. P. Curran, Tetrahedron, 2002, 58, 3855-3864.

DOI: 10.1016/S0040-4020(02)00205-3


A fully fluorous Mitsunobu reaction employing a fluorous phosphine and a fluorous azodicarboxylate is described. Pure products can be isolated by rapid solid phase extraction (spe) over fluorous silica in excellent yields. The fluorous fraction containing the flourous phosphine oxide and the flourous hydrazide can be separated and the starting reagents can be regenerated using appropriate redox reactions.

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Second Generation Fluorous DEAD Reagents Have Expanded Scope in the Mitsunobu Reaction and Retain Convenient Separation Features

S. Dandapani, D. P. Curran, J. Org. Chem., 2004, 69, 8751-8757.

DOI: 10.1021/jo0488098

Key Words

fluorous, Mitsunobu reaction, solid phase extraction, triphenylphosphine, diethylazodicarboxylate, Phthalimides

ID: J72-Y2002-110