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Green Chemistry
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The reaction mixture was left stirring for 18 hours at room 11 For the use of Ti, see: a) K. Miura, A. Hosomi, VSieywnAlerttictle2O0n0lin3e,
DOI: 10.1039/C6GC02580C
temperature and then aqueous HCl (1N) (1.0 mL, 1.00 mmol) was
added and the reaction mixture was stirred for 2 hours. Then,
EtOAc (20 mL) was added into the mixture and the organic layer
was washed with HCl 1N (10 mL) and brine (10 mL), dried over
Na2SO4, filtered and concentrated in vacuo. If the product required
further purification, filtration through a short silica plug was
performed (30-50% EtOAc in Pet. Ether).
143; For the use of Co, see: b) C. Palmer, N. A. Morra, A. C.
Stevens, B. Bajtos, B. P. Machin, B. L. Pagenkopf, Org. Lett.
2009, 11, 5614; c) G. A. Phillips, C. Palmer, A. C. Stevens, M. L.
Piotrowski, D. S. R. Dekruyf, B. L. Pagenkopf, Tetrahedron Lett.
2015, 56, 6052; d) H. Shigehisa, M. Hayashi, H. Ohkawa, T.
Suzuki, H. Okayasu, M. Mukai, A. Yamazaki, R. Kawai, H.
Kikuchi, Y. Satoh, A. Fukuyama, K. Hiroya, J. Am. Chem. Soc.
2016, DOI: 10.1021/jacs.6b05720.
12 For the use of Zn, see: a) T. J. Donohoe, O. Williams, G. H.
Churchill, Angew. Chem. Int. Ed. 2008, 47, 2869; For the use of
Acknowledgements
The authors would like to thank Dr. Maroula Kokotou for her
assistance in acquiring HRMS data.
Ir, see: b) M. Rueping, V. B. Phapale, Green Chem. 2012, 14
,
55; For the use of Cu, see: c) Y. Miller, A. S. Hosseini, S. R.
Chemler, J. Am. Chem. Soc. 2012, 134, 12149; d) S. M. Nicolle,
W. Lewis, C. J. Hayes, C. J. Moody, Angew. Chem. Int. Ed. 2015,
54, 8485; For the use of Rh, see: e) C. Jing, D. Xing, L. Gao, J. Li,
W. Hu, Chem. Eur. J. 2015, 21, 19202; For the use of Pd, see: f)
J. P. Wolfe, M. A. Rossi, J. Am. Chem. Soc. 2004, 126, 1620; g)
Notes and references
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9
For selected reviews on synthetic approaches to
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1965, 21, 2353; b) J. E. Baldwin, M. J. Crossley, E.-M. M.
Lehtoven, J. Chem. Soc. Chem. Commun. 1979, 918; For the
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5238.
20 The structure of the active oxidant of the oxidation protocol is
still unknown. The possibility of a dioxirane intermediate
cannot be ruled out.
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