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K. E. Coffey, G. K. Murphy
Synpacts
Synlett
Acknowledgment
(13) (a) Kim, J. J.; Kweon, D. H.; Cho, S. D.; Kim, H. K.; Lee, S. G.; Yoon,
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2013, 5376. For an example using PhICl2, see: (d) Duan, X.;
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This work was supported by NSERC of Canada and the University of
Waterloo. We also wish to thank the Mass Spectrometry Facility at
the University of Waterloo for sample analysis.
Supporting Information
(15) Lee, K. I.; Youn, J. I.; Shim, Y. K.; Kim, W. J. Bull. Korean Chem.
Soc. 1992, 13, 226.
(16) Olah, G. A.; Welch, J. Synthesis 1974, 896.
Supporting information for this article is available online at
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(17) Yusubov, M. S.; Zhdankin, V. V. Curr. Org. Synth. 2012, 9, 247.
(18) (a) Sket, B.; Zupan, M.; Zupet, P. Tetrahedron 1984, 40, 1603.
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hedron Lett. 2011, 52, 1952.
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(22) Kitamura, T.; Tazawa, Y.; Morshed, M. H.; Kobayashi, S. Synthesis
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(24) Caution: Diazo compounds are reported to be toxic and poten-
tially explosive. Appropriate safety measures should be
observed when working with them.
(25) (a) Regitz, M.; Maas, G. Diazo Compounds: Properties and Syn-
thesis; Academic Press: Orlando, 1986, xi. (b) Doyle, M. P.;
Mckervey, M. A.; Ye, T. Modern Catalytic Methods for Organic
Synthesis with Diazo Compounds : From Cyclopropanes to Ylides;
Wiley: New York, 1998, 652.
(26) Bug, T.; Hartnagel, M.; Schlierf, C.; Mayr, H. Chem. Eur. J. 2003, 9,
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(27) Abel, E. W.; Stone, F. G. A.; Wilkinson, G. Comprehensive Organo-
metallic Chemistry II: A Review of the Literature 1982–1994; Per-
gamon Press: Oxford, 1995, 1st ed..
(28) In carbenoid reactions, elevated temperatures are required for
diazo Meldrum’s acid to react. See: (a) Somai Magar, K. B.; Lee,
Y. R.; Kim, S. H. Tetrahedron 2013, 69, 9294. (b) Shi, J.; Yan, Y.; Li,
Q.; Xu, H. E.; Yi, W. Chem. Commun. 2014, 50, 6483.
(29) For example, chlorination of 23d using 5 mol% DMAP or 2,6-
lutidine, or either 1 mol% or 10 mol% pyridine gave mixtures of
24d/25d. The best improvement came from using 5 mol% pyri-
dine in DCE, which gave 24d in 51% yield. However, chlorinating
23a in DCE gave 24a in only 43% yield, so this effect was not
pursued.
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