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Fluorous Mitsunobu reagents and reactions

Dandapani, S and Curran, DP (2002) Fluorous Mitsunobu reagents and reactions. Tetrahedron, 58 (20). 3855 - 3864. ISSN 0040-4020

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Abstract

A fully fluorous Mitsunobu reaction procedure is introduced. This employs both existing [(C6F13CH2CH2C6H 4)2PPh] and new [C8F17CH2CH2C6H 4PPh2] fluorous phosphines and a new fluorous azodicarboxylate (C6F13CH2CH2OC(O)N=NCOOCH 2CH2C6F13). A procedure involving parallel reactions with representative nucleophiles and alcohols under typical Mitsunobu conditions in THF followed by rapid solid phase extraction (spe) over fluorous silica provides clean products in excellent yields. The fluorous fraction containing the oxidized phosphine oxide and the reduced hydrazide can be readily separated and the starting reagents can be regenerated by appropriate redox reactions in high yield for reuse. © 2002 Elsevier Science Ltd. All rights reserved.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Dandapani, S
Curran, DPcurran@pitt.eduCURRAN
Date: 13 May 2002
Date Type: Publication
Journal or Publication Title: Tetrahedron
Volume: 58
Number: 20
Page Range: 3855 - 3864
DOI or Unique Handle: 10.1016/s0040-4020(02)00205-3
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0040-4020
Date Deposited: 13 Feb 2014 18:55
Last Modified: 30 Mar 2019 14:55
URI: http://d-scholarship.pitt.edu/id/eprint/20506

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