Dennis P. Curran et al.
FULL PAPERS
layer was then washed thrice with a 2:1 mixture of HFE-
7100 and FC-72 (7 mL). The organic layer was then diluted
with water (20 mL) and the product was extracted into ether
(310 mL). The combined organic layer was then washed
with saturated sodium bicarbonate solution (210 mL) and
with brine (210 mL). The solvent was evaporated under
vacuum to give the product (20.3 mg) as yellow oil.
Paul, C. J. Gabriel, J. R. Parquette, Chemtracts 2002,
15, 617–622.
[5] Introduction of fluorous Mitsunobu reagents: a) A. P.
Dobbs, C. McGregor-Johnson, Tetrahedron Lett. 2002,
43, 2807–2810; b) S. Dandapani, D. P. Curran, Tetrahe-
dron 2002, 58, 3855–3864; fluorous nucleophiles:
c) M. W. Markowicz, R. Dembinski, Org. Lett. 2002, 4,
3785–3787; fluorous alcohols: d) J. Rabai, D. Szabo,
E. K. Borbas, I. Kovesi, I. Kovesdi, A. Csampai, A.
Gomory, V. E. Pashinnik, Y. G. Shermolovich, J. Fluo-
rine Chem. 2002, 114, 199–207; e) A.-M. Balint, A.
Bodor, A. Gomory, K. Vekey, D. Szabo, J. Rabai, J.
Fluorine Chem. 2005, 126, 1524–1530.
Supporting Information
1
Contains copies of H and 19F NMR spectra and GC chro-
[6] Dobbs and McGregor-Johnson (ref.[5a]) have reported
matograms for all the crude products in Figure 2.
that the hydrazide derived from C6F13
A
NCO2(CH2)3C6F13 can be removed by partitioning be-
AHCTREUNG
tween FC-72 and CH2Cl2. Partition coefficients for this
diazodicarboxylate and the derived hydrazide are in
the M. Sc. Thesis of C. McGregor-Johnson, University
of Exeter, 2003. We kindly thank A. Dobbs for provid-
ing this information.
Acknowledgements
We thank the National Institutes of Health (National Institute
for General Medical Sciences) for funding of this work. ES
thanks the National Science Foundation Research Experience
for Undergraduates (REU) program for a fellowship.
[7] Currently preferred reagents and procedure for Mitsu-
nobu reaction with fluorous spe separation: S. Danda-
pani, D. P. Curran, J. Org. Chem. 2004, 69, 8751–8757.
[8] Each reagent was partitioned between the two solvents
with vigorous stirring for 15 min, then small amounts of
each layer were injected into GC in triplicate. The par-
tition coefficients were derived from the ratios of the
absolute area counts of each layer.
[9] Reviews of fluorous solvents: a) J. A. Gladysz, C.
Emnet, in: Handbook of Fluorous Chemistry, (Eds.:
J. A.Gladysz, D. P. Curran, I. T. Horvath), Wiley-VCH,
Weinheim, 2004, p 11–23; b) I. Ryu, H. Matsubara, C.
Emnet, J. A. Gladysz, S. Takeuchi, Y. Nakamura, D. P.
Curran, in: Green Reaction Media in Organic Synthesis
(Ed.: K. Mikami), Blackwell, Oxford, 2005, p 59–124.
[10] M. S. Yu, D. P. Curran, T. Nagashima, Org. Lett. 2005,
7, 3677–3680.
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[11] HFE-7100 and FC-72 are available from 3M and other
sources. The reagents are sold by Fluorous Technolo-
gies, Inc., Aldrich, Fluka, and Waco (in Japan). DPC
owns an equity interest in Fluorous Technologies.
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