Page 5 of 6
COMMUNICATION
New Journal of Chemistry
DOI: 10.1039/C4NJ00941J
168.5 (
C
=N), 157.8 (
C
ꢀOH), 151.3 (
ꢀH), 52.2 (
= 14.1 Hz). ESI(+)ꢀMS: 387.1
C
quat), 138.4 (
CꢀH), 132.6
(
CꢀH), 120.1 (
CꢀH), 118.1 (
C
J
C
ꢀH2). 19F NMR (282
MHz, DMSO) δ ꢀ158.15 (q,
[M+Na]+.
Complex
3
=
3,3'-(ethane-1,2-diyl)bis(2,2-difluoro-6-
benzhydryl-2H-benzo[e][1,3,2]oxazaborinin-3-ium-2-uide)
42 mg, yield quant. mp 185ꢀ187 °C. 1H NMR (300 MHz,
3
4
CDCl3, 25 ºC):
2.1 Hz, 2H, aromatic C
7.12ꢀ6.90 (m, 12H, aromatic C
4H, CH2). 13C NMR (75 MHz, CDCl3) δ 167.5 (
ꢀOH), 142.3 (2 X ꢀH), 140.5 ( ꢀH), 136.4 ( ꢀH), 132.0 (
H), 129.2 (4 X ꢀH), 128.6 (4 X ꢀH), 126.80 (2 X ꢀH), 119.3
quat), 114.9 ( quat), 55.6 ( ꢀH), 54.1 (
ꢀH2). 19F NMR (282
δ
8.25 (s, 2H, C
), 7.34ꢀ7.16 (m, 12H, aromatic C
), 5.45 (s, 2H, C ), 4.29 (s,
=N), 158.0
H
N), 7.40 (dd, JHꢀH 8.7, JHꢀH
H
H
),
H
H
C
1
2
(
C
C
C
C
Cꢀ
R. Barth, M. G. Vicente, O. Harling, W. Kiger, K. Riley, P. Binns, F.
C
C
C
C
Wagner, M. Suzuki, T. Aihara, I. Kato, S. Kawabata, Radiat. Oncol.,
(
C
C
C
2012,
M. Suginome, L. Uehlin, A. Yamamoto, M. Murakami, Org. Lett.,
2004, , 1167.
7, 146.
MHz, ) δ ꢀ158.56 (bs). ESI(+)ꢀMS: 677.3 [MꢀF]+, 719.2
[M+Na]+.
6
3 J. W. J. Kennedy, D. G. Hall, Angew. Chem. Int. Ed., 2003, 42, 4732.
Complex
4 = 3,3'-(ethane-1,2-diyl)bis(2,2-difluoro-6-trityl-2H-
4
F. D'Souza, P. M. Smith, M. E. Zandler, A. L. McCarty, M. Itou, Y.
benzo[e][1,3,2]oxazaborinin-3-ium-2-uide)
21 mg, yield 95%. mp > 300 °C. H NMR (300 MHz, CDCl3,
1
Araki, O. Ito, J. Am. Chem. Soc., 2004, 126, 7898.
5
3
4
V. Barba, H. Hopfl, N. Farfan, R. Santillan, H. I. Beltran, L. S.
25 ºC):
2H, aromatic C
(m, 12H, aromatic C
), 4.29 (s, 4H, CH2). 13C NMR (75 MHz, CDCl3, 25ºC): δ
δ
8.23 (s, 2H, C
H
N), 7.40 (dd, JHꢀH 8.9, JHꢀH 2.2 Hz,
), 7.16ꢀ7.06
), 6.97 (d, JHꢀH 8.9 Hz, 2H, aromatic
ZamudioꢀRivera, Chem. Commun., 2004, 2834.
H
), 7.33ꢀ7.15 (m, 20H, aromatic C
H
6
3
K. Ma, M. Scheibitz, S. Scholz, M. Wagner, J. Organomet. Chem.,
H
2002, 652, 11.
CH
7
G. Wu, R. F. Barth, W. Yang, M. Chatterjee, W. Tjarks, M. J.
167.5 (
139.4 (
C
C
=N), 157.9 (
ꢀH), 132.3 (
ꢀH), 118.4 (
C
C
ꢀOH), 145.8 (3 X
ꢀH), 130.8 (6 X ꢀH), 127.8 (6 X
quat), 114.0 ( quat), 64.0 (
C
quat), 143.5 (
C
C
quat),
ꢀH),
ꢀH),
Ciesielski, R. A. Fenstermaker, Bioconjugate Chem., 2003, 15, 185.
C
8
G.ꢀL. Fu, H. Pan, Y.ꢀH. Zhao, C.ꢀH. Zhao, Org. Biomol. Chem., 2011,
126.4 (3 X
54.1 (
C
C
C
C
C
ꢀH2). 19F NMR (282 MHz, CDCl3) δ ꢀ158.10 (bs).
9, 8141.
9
ESI(+)ꢀMS: 829.3 [MꢀF]+, 871.3 [M+Na]+.
J.ꢀB. Wang, Q.ꢀQ. Wu, Y.ꢀZ. Min, Y.ꢀZ. Liu, Q.ꢀH. Song, Chem.
Commun., 2012, 48, 744.
10 C. Zhao, Y. Zhang, P. Feng, J. Cao, Dalton Trans., 2012, 41, 831.
Acknowledgements
11
T.ꢀI. Kim, J. Park, S. Park, Y. Choi, Y. Kim, Chem. Commun., 2011,
47, 12640.
Thanks are due to the University of Aveiro and the Portuguese
Fundação para a Ciência e a Tecnologia (FCT), EU, QREN, FEDER
and COMPETE for funding the Organic Chemistry Research Unit
(project PEstꢀC/QUI/UI0062/2013), the CICECO Associate
Laboratory (PEstꢀC/CTM/LA0011/2013) and the Portuguese
National NMR Network (RNRMN). SG also thanks the FCT for a
postdoctoral grant (SFRH/BPD/70702/2010).
12
S. ErtenꢀEla, M. D. Yilmaz, B. Icli, Y. Dede, S. Icli, E. U. Akkaya,
Org. Lett., 2008, 10, 3299.
13
Y. Zhou, J. W. Kim, R. Nandhakumar, M. J. Kim, E. Cho, Y. S. Kim,
Y. H. Jang, C. Lee, S. Han, K. M. Kim, J.ꢀJ. Kim, J. Yoon, Chem.
Commun., 2010, 46, 6512.
14 F. Umland, E. Hohaus, K. Brodte, Chem. Ber., 1973, 106, 2427.
15
K. Tanaka, T. Tsuchitani, N. Fukuda, A. Masumoto, R. Arakawa,
Tetrahedron: Asymmetry, 2012, 23, 205.
Notes and references
16
G. Vargas, I. Hernández, H. Höpfl, M.ꢀE. Ochoa, D. Castillo, N.
Farfán, R. Santillan, E. Gómez, Inorg. Chem., 2004, 43, 8490.
17 D. A. Atwood, M. J. Harvey, Chem. Rev., 2000, 101, 37.
18 P. Wei, D. Atwood, Chem. Commun., 1997, 1427.
* Corresponding authors; eꢀmail: sguieu@ua.pt, artur.silva@ua.pt
a
QOPNA, Department of Chemistry, University of Aveiro, 3810ꢀ193
Aveiro, Portugal.
19 J. M. Rivera, S. Rincón, N. Farfán, R. Santillan, J. Organomet. Chem.,
b
CICECO, Department of Chemistry, University of Aveiro, 3810ꢀ193
2011, 696, 2420.
Aveiro, Portugal.
20 D. Frath, S. Azizi, G. Ulrich, P. Retailleau, R. Ziessel, Org. Lett., 2011, 13,
3414.
† CCDCꢀ1006070, 1006071 and 1017586 contain the supplementary
crystallographic data for this paper. These data can be obtained free of
Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge
21 F. Cardona, J. Rocha, A. M. S. Silva, S. Guieu, Dyes and Pigments, 2014,
111, 16.
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CB2
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UK.
Fax:
C44
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336
033.
Eꢀmail:
23 Y. Hong, J. W. Y. Lam, B. Z. Tang, Chem. Commun., 2009, 4332.
deposit@ccdc.cam.ac.uk).
24 Y. Hong, J. W. Y. Lam, B. Z. Tang, Chem. Soc. Rev. 2011, 40, 5361
.
Electronic Supplementary Information (ESI) available: [Experimental
procedures, compound characterization data and NMR spectra of the new
compounds]. See DOI: 10.1039/c000000x/.
25
H. Oie, A. Sudo, T. Endo, J. Polym. Sci., Part A: Polym. Chem., 2011,
49, 3174.
4 | New J. Chem., 2014, 00, 1-3
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