Organic Letters
Letter
(10) Jaganathan, A.; Staples, R. J.; Borhan, B. J. Am. Chem. Soc. 2013,
135, 14806.
Scheme 1. Gram Scale Chlorocyclizations Using
Chloramine-T·3H2O/(DHQD)2PHAL
(11) The effect of the weakly coordinating counteranion with HFIP
is not readily reproduced with other protic additives that possess
similar pKa values. For an elegant example illustrating the effect of the
counteranion on the enantioselectivity in an analogous iodocyclization
reaction, see: Dobish, M. C.; Johnston, J. N. J. Am. Chem. Soc. 2012,
134, 6068.
(12) (a) Li, G.; Angert, H. H.; Sharpless, K. B. Angew. Chem., Int. Ed.
1996, 35, 2813. (b) Rudolph, J.; Sennhenn, P. C.; Vlaar, C. P.;
Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2810. (c) Vyas,
R.; Chanda, B. M.; Bedekar, A. V. Tetrahedron Lett. 1998, 39, 4715.
(13) Morris, J. C.; Salazar, J. A.; Wineman, M. A. J. Am. Chem. Soc.
1948, 70, 2036.
(14) Higuchi, T.; Hussain, A. J. Chem. Soc. B 1967, 549.
(15) In our attempts to synthesize this compound from TsNH2, we
have been able to observe this species in solution by NMR analysis in
CDCl3 along with unreacted TsNH2 and over chlorinated TsNCl2.
This species has been invoked as the putative chlorenium source in an
unrelated intermolecular chloroamination reaction of chalcones; for an
example, see: Cai, Y.; Liu, X.; Jiang, J.; Chen, W.; Lin, L.; Feng, X. J.
Am. Chem. Soc. 2011, 133, 5636.
ASSOCIATED CONTENT
* Supporting Information
Experimental procedures and spectroscopic data. This material
■
S
(16) Evans, J. C.; Jackson, S. K.; Rowlands, C. C.; Barratt, M. D.
Tetrahedron 1985, 41, 5191.
AUTHOR INFORMATION
Corresponding Author
■
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
This work was funded by the NSF grant CHE-0957462.
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