European Journal of Inorganic Chemistry
10.1002/ejic.201900165
COMMUNICATION
4
47-449 e) R. Bohlmann, D. Bittler; M. Gottwald, P. Muhn,
CCDC-1892768 contains supplementary crystallographic data
for this compound. These data can be obtained free of charge
from The Cambridge Crystallographic Data Centre via
www.ccdc.cam.ac.uk/data_request/cif.
Y. Nishino, B. Schoenecker, G. Hobe, DE 4330237 A1,
Germany, 1995.
R. M. Kaul, J. Ernest, J. Sun, D. Vocadlo, Y. Zhou, Y. Zhu,
WO 2015095963 A1, Alectos Therapeutics Inc., Can,
[
[
[
13]
14]
15]
2
015.
M. F. Deodhar, D. Alison, J. S. Foot, W. Jarolimek, I. A.
Mcdonald, A. Robertson, C. I. Turner, WO 2013163675 A1,
Pharmaxis Ltd., Australia, 2013.
Acknowledgements
a) D. J. Burton, D. M. Wiemers, J. Fluorine Chem. 1985,
2
7, 85-89 b) G. Landelle, J.-F. Paquin, e-EROS Encycl.
We are thankful to F-Select GmbH for a generous donation of
CH FI. We thank Prof. Dr. T. M. Klapötke for the generous
2
allocation of diffractometer time and for his continuous support.
We thank Thomas Schnappinger for the help with the DFT
calculations.
Reagents Org. Synth., John Wiley & Sons, Ltd, Chichester,
UK, 2011 c) D. G. Cox, D. J. Burton, J. Org. Chem. 1988,
5
1969, Thieme, Stuttgart, 75 - 76.
D. J. Burton, P. E. Greenlimb, J. Org. Chem. 1975, 40,
3, 366-374 d) M. Schlosser, M. Zimmermann, Synthesis
[
[
[
[
16]
17]
18]
19]
2
796.
J. Adamek, J. Mrowiec-Białoń, A. Październiok-Holewa, R.
Mazurkiewicz, Thermochim. Acta 2011, 512, 22-27.
F. H. Allen, D. G. Watson, L. Brammer, A. G. Orpen, R.
Taylor, J. Chem. Soc., Perkin Trans. 2 1987, 1 - 19.
M. Feller, K. Lux, A. Kornath, Eur. J. Inorg. Chem. 2015,
Keywords: fluoromethylation • fluoroiodomethane • synthesis •
phosphonium salt • crystal structure
[
[
[
[
[
[
1]
2]
3]
4]
5]
6]
W. Zhang. J. Hu, F. Wang, Chem. Commun. 2009, 7465 -
478.
D. K. Kölmel, Chemische Biologie von Peptoiden und
Synthese fluoriger Farbstoffe, Vol. 25, Logos, Berlin, 2013.
G. K. S. Prakash, I. Ledneczki, S. Chacko, G. A. Olah,
Org. Lett. 2008, 10, 557-560.
5
357.
7
[
[
[
20]
21]
22]
C. Siebert, Chem. Unserer Zeit 2004, 38.
M.C Davis, D. A. Parrish, Synth. Commun. 2008, 38, 3909.
a) M. Hesse, H. Meier, B. Zeeh, Spektroskopische
Methoden in der organischen Chemie, Thieme, 2005 b) A.
F. Izmaylov, G. Zheng, J. L. Sonnenberg, M. Hada, , K. T.
M. Ehara, R. Fukuda, J. Hasegawa, M. Ishida, T.
Nakajima, , O. K. Y. Honda, H. Nakai, T. Vreven, J. A.
Montgomery, Jr., , F. O. J. E. Peralta, M. Bearpark, J. J.
Heyd, E. Brothers, , V. N. S. K. N. Kudin, T. Keith, R.
Kobayashi, J. Normand, , A. R. K. Raghavachari, J. C.
Burant, S. S. Iyengar, J. Tomasi, , N. R. M. Cossi, J. M.
Millam, M. Klene, J. E. Knox, J. B. Cross, , C. A. V.
Bakken, J. Jaramillo, R. Gomperts, R. E. Stratmann, , A. J.
A. O. Yazyev, R. Cammi, C. Pomelli, J. W. Ochterski, , K.
M. R. L. Martin, V. G. Zakrzewski, G. A. Voth, , J. J. D. P.
Salvador, S. Dapprich, A. D. Daniels, , J. B. F. O. Farkas,
J. V. Ortiz, J. Cioslowski, , a. D. J. Fox, Gaussian, Inc.,
Wallingford CT, 2010.
Program package CrysAlisPro 1.171.38.46 Rigaku OD,
2
G. M. Sheldrick, SHELXS-97: Program for Crystal
Structure Solution, University of Göttingen, Germany,
1
G. M. Sheldrick, SHELXL-97: Program for the Refinement
of Crystal Structures, University of Göttingen, Germany,
1
A. L. Spek, PLATON: A Multipurpose Crystallographic
Tool, Utrecht University, Utrecht, The Netherlands, 1999.
J. Hu, B. Gao, L. Li, C. Ni, J. Hu, Org. Lett. 2015, 17,
3
086-3089.
T. Ochiai, R. Ishida, Jpn. J. Pharmacology 1982, 32, 427-
38.
4
L. V. Kudzma, C. G. Huang, R. A. Lessor, L. A. Rozov, S.
Afrin, F. Kallashi, C. McCutcheon, K. Ramig, J. Fluorine
Chem. 2001, 111, 11-16.
[
[
7]
8]
a) C. Walsh, Tetrahedron 1982, 38, 871-909; b) T.
Tsushima, K. Kawada, Tetrahedron Lett. 1985, 26, 2445-
2
448.
R. Bohlmann, DE 4330237 A1 (Ed.: S. AG), Germany,
995.
1
[
[
9]
10]
S. Monticelli, V. Pace, Aust. J. Chem. 2018, 71, 473-475.
G. Parisi, M. Colella, S. Monticelli, G. Romanazzi, W.
Holzer, T. Langer, L. Degennaro, V. Pace, R. Luisi, J. Am.
Chem. Soc. 2017, 139, 13648-13651.
[
[
23]
24]
015.
[
[
11]
12]
a) J. Veliks, A. Kazia, Chem Eur. J. 2019, 25, 3786-3789;
b) S. Monticelli, M. Colella, V. Pillari, A. Tota, T. Langer, W.
Holzer, L. Degennaro, R. Luisi, V. Pace, Org. Lett. 2019,
997.
[
[
25]
26]
2
1, 584-588.
a) M. Zhou. X. Shen , C. Ni, W. Zhang, J. Hu Chem. Sci.
014, 5, 117 - 122 b) F. Swarts, Bull. Cl. Sci., Acad. R.
Belg. 1910, 113 - 123 c) E. P. T. Leitao, C. R. Turner, WO
011151624 A1, Hovione Inter Limited, Switz, 2011 d) D.
J. Burton, P. E. Greenlimb, J. Fluorine Chem. 1974, 3,
997.
2
2
This article is protected by copyright. All rights reserved.