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X-ray crystallography
Single-crystal diffraction experiments were conducted on a
Bruker APEX-II CCD diffractometer (13,14, 15b, 29 and 30)
and an Xcalibur Sapphire3 diffractomer (19), using Mo Kα ra-
diation. Crystals were cooled using Cryostream (Oxford
Cryosystems) open-flow N2 cryostats. The structures were
solved within Olex2 by direct methods and refined by full-
matrix least squares against F2 of all data, using SHELXTL
software [33-37]. All non-hydrogen atoms were refined
anisotropically. Hydrogen atom positions were calculated
geometrically and refined using the riding model. CCDC
(1433617–1433622) contains the supplementary crystallo-
graphic data for this paper. The data can be obtained free of
charge from The Cambridge Crystallographic Data Centre via
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Supporting Information
Supporting information features full synthetic procedures,
in situ FTIR data plots, copies of 1H, 13C and 11B NMR
spectra, and full crystallographic data including images and
CIF files.
10.Sánchez, I.; Pujol, M. D. Synthesis 2006, 1823–1828.
11.Birch, A. J.; Lehman, P. G. J. Chem. Soc., Perkin Trans. 1 1973,
12.Smith, W. H.; Bard, A. J. J. Am. Chem. Soc. 1975, 97, 6491–6495.
Supporting Information File 1
13.Li, Y.-M.; Shen, Y.; Chang, K.-J.; Yang, S.-D. Tetrahedron Lett. 2014,
Full synthetic procedures, in situ FTIR data plots, and
copies of 1H, 13C and 11B NMR spectra.
14.Barnard, J. H.; Zhou, G.-L.; Collings, J. C.; Whiting, A.; Marder, T. B.
Durham University, Durham, UK, Unpublished work.
15.Koo, J. J. Am. Chem. Soc. 1953, 75, 1891–1895.
16.Monnereau, C.; Blart, E.; Odobel, F. Tetrahedron Lett. 2005, 46,
Supporting Information File 2
Crystallographic Information Files of compounds 13, 14,
15b, 19, 29, and 30.
17.Emmanuvel, L.; Shukla, R. K.; Sudalai, A.; Gurunath, S.; Sivaram, S.
Tetrahedron Lett. 2006, 47, 4793–4796.
18.Kawade, R. K.; Huple, D. B.; Lin, R.-J.; Liu, R.-S. Chem. Commun.
19.Tomcufcik, A. S.; Seeger, D. R. J. Org. Chem. 1961, 26, 3351–3356.
Acknowledgements
20.Castanet, A.-S.; Colobert, F.; Broutin, P.-E. Tetrahedron Lett. 2002, 43,
DRC thanks the EPSRC, BBSRC and High Force Research Ltd.
for doctoral funding. GLZ also thanks the EPSRC and High
Force Research Ltd. for doctoral funding. We thank Helen
Osborne and Prof. Todd B. Marder for helpful discussions, Dr.
Horst Puschmann for general crystallographic guidance and for
assistance in the solution of the crystal structure of 19, and Dr.
Dmitry S. Yufit for general crystallographic guidance.
21.Adimurthy, S.; Ramachandraiah, G.; Ghosh, P. K.; Bedekar, A. V.
Tetrahedron Lett. 2003, 44, 5099–5101.
22.Yamamoto, T.; Toyota, K.; Morita, N. Tetrahedron Lett. 2010, 51,
23.Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124,
24.Thompson, M. D.; Berlin, K. D. Proc. Okla. Acad. Sci. 1985, 65, 39–43.
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