Organic Letters
Letter
(17) Luzung, M. R.; Patel, J. S.; Yin, J. J. Org. Chem. 2010, 75, 8330−
8332.
Research Fellowship under Grant 1122374. The Varian 300
and 500 MHz NMR spectrometers used for portions of this
work were purchased with funds from NSF (Grants CHE-
9808061 and DBI-9729592). The authors thank Dr. Yiming
Wang (MIT) for help in preparing this article.
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(15) The more reactive nucleophile 2-pyridylmagnesium chloride
afforded only an 11% yield of the desired sulfonate ester 4a upon
treatment with TCPC at −78 °C. Under the same reaction conditions,
2-pyridyllithium also resulted in a low yield of 4a (<10%).
(16) Kristensen11e reported that 2 can react with pentafluorophenol
in the presence of triethylamine to form pentafluorophenyl pyridine-2-
sulfonate in 76% yield.
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