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Dalton Transactions
Page 9 of 10
DOI: 10.1039/C6DT04534K
Journal Name
ARTICLE
12 E. M. Leitao, S. R. Dubberley, W. E. Piers, Q. Wu, R.
McDonald, Chem. Eur. J., 2008, 14, 11565.
13 M. S. Viciu, R. F. Germaneau, O. Navarro-Fernandez, E. D.
Stevens, S. P. Nolan, Organometallics, 2002, 21, 5470.
14 N. Marion, O. Navarro, J. Mei, E. D. Stevens, N. M. Scott, S. P.
Nolan, J. Am. Chem. Soc., 2006, 128, 4101.
15 M. G. Organ, S. Avola, I. Dubovyk, N. Hadei, E. A. B. Kantchev,
C, J. O’Brien, C. Valente, Chem. Eur. J., 2006, 12, 4749.
16 G. Altenhoff, R. Goddard, C. W. Lehmann, F. Glorius, J. Am.
Chem. Soc., 2004, 126, 15195.
17 S. Wuertz, C. Lohre, R. Froehlich, K. Bergander, F. Glorius, J.
Am. Chem. Soc., 2009, 131, 8344.
18 a) X. Luan, R. Mariz, M. Gatti, C. Constabile, A. Poater, L.
transformed into their corresponding iridium-dicarbonyl
species and used to analyse the electronic properties of the
ligands. The incorporation of the 2-morpholinonaphthyl and 2-
piperidinylnaphthyl groups had the effect of providing ligands
of overall slightly more electronic-donating nature, with the
piperidyl ligand showing TEP values normally found for alkyl-
substituted NHC ligands (e.g. ICy).
Catalytic results with NHC-palladium and NHC-GII compounds
were rather disappointing. The NHC-palladium complexes
showed overall poor catalytic performance for this class of
(pre)catalysts. When used as catalysts in Suzuki-Miyaura
coupling reactions, they only provided good reactivity with the
simplest chloro- and bromoarene substrates at room
temperature. With the NHC-GII precatalysts as applied to
representative ring-closing metathesis reactions of dienes and
enynes, we only observed reasonable activity when running
the reactions at elevated temperature (60°C) with toluene as
the solvent. We believe that these results indicate that the
second, hemilabile binding point of these ligands (morpholine,
piperidine) is able to degrade the active catalyst species much
more easily in the catalytic applications chosen here. The
ligands we synthesised here should nevertheless prove useful
in catalytic applications where such hemilability is essential for
good catalytic activity and pertinent studies are underway in
our laboratories.
Cavallo, A. Linden, R. Dorta, J. Am. Chem. Soc., 2008, 130
,
6848. b) L. Vieille-Petit, X. Luan, R. Mariz, S. Blumentritt, A.
Linden, R. Dorta, Eur. J. Inorg. Chem., 2009, 1861. c) L.
Vieille-Petit, X. Luan, M. Gatti, S. Blumentritt, A. Linden, H.
Clavier, S. P. Nolan, R. Dorta, Chem. Commun., 2009, 3783. d)
L. Vieille-Petit, H. Clavier, A. Linden, S. Blumentritt, S. P.
Nolan, R. Dorta, Organometallics, 2010, 29, 775. e) L. Wu, E.
Drinkel, F. Gaggia, S. Capolicchio, A. Linden, L. Falivene, L.
Cavallo, R. Dorta, Chem. Eur. J., 2011, 17, 12886. f) G. Sipos,
A. Ou, B. W. Skelton, L. Falivene, L. Cavallo, R. Dorta, Chem.
Eur. J., 2016, 22, 6939.
19 a) X. Luan, R. Mariz, C. Robert, M. Gatti, S. Blumentritt, A.
Linden, R. Dorta, Org. Lett., 2008, 10, 5569.; b) X. Luan, L.
Wu, E. Drinkel, R. Mariz, M. Gatti, R. Dorta, Org. Lett., 2010,
12, 1912.; c) L. Wu, L. Falivene, E. Drinkel, S. Grant, A. Linden,
L. Cavallo, R. Dorta, Angew. Chem. Int. Ed., 2012, 124, 2924.
20 L. Wu, A. Salvador, A. Ou, M. W. Shi, B. W. Skelton, R. Dorta,
Synlett, 2013, 24, 1215.
21 Various chelating NHC structures that rely on the same
design (additional ligation through the ortho position of aryl
wingtips) have been successful, see: N-Heterocyclic Carbenes
4. Acknowledgements
AO thanks the Australian Government and UWA for a
postgraduate scholarship. RD thanks the Australian Research
council for funding (FT130101713). The Centre for Microscopy,
Characterisation & Analysis at UWA is thanked for providing
facilities and assistance.
(Ed.: S. P. Nolan), Wiley-VCH: Weinheim, 2014
22 For representative examples: a) R. J. Lundgren, B. D. Peters,
P. G. Alsabeh, M. Stradiotto, Angew. Chem. Int. Ed., 2010, 49
.
,
4071. b) R. J. Lundgren, M. Stradiotto, Angew. Chem. Int. Ed.,
2010, 49, 8686. c) K. D. Hesp, R. J. Lundgren, M. Stradiotto, J.
Am. Chem. Soc., 2011, 133, 5194.
23 M. Gatti, L. Wu, E. Drinkel, F. Gaggia, S. Blumentritt, A.
Linden, R. Dorta, Arkivoc, 2011, 176.
24 Crystallographic data for the structures reported in this
paper have been deposited at the Cambridge
Crystallographic Data Centre with supplementary publication
numbers given below. Copies of the data can be obtained
free of charge on application to CCDC, 12 Union Rd,
Cambridge CB21EZ, UK (fax +441223336033; email
structure refinement data are summarized in the Supporting
Information. CCDC files 1518956-1518966 contain
crystallographic data for the crystal structures reported
herein.
25 A. J. Arduengo III, R. Krafczyk, R. Schmutzler, H. A. Craig, A.
Hugh, J. R. Goerlich, W. J. Marshall, M. Unverzagt,
Tetrahedron, 1999, 55, 14523.
26 A. J. Arduengo III, J. R. Goerlich, W. J. Marshall, J. Am. Chem.
Soc., 1995, 117, 11027.
5. Notes and references
1
J. E. Hill, T. A. Nile, J. Organomet. Chem., 1977, 137, 293.
M. F. Lappert, R. K. Maskell, J. Organomet. Chem., 1984, 264
217.
2
3
4
5
6
7
8
9
,
A. J. Arduengo III, R.L. Harlow, M. J. Kline, J. Am. Chem. Soc.,
1991, 113, 361.
W. A. Herrmann, M. Elison, J. Fischer, C. Kocher, G. R. J.
Artus, Angew. Chem. Int. Ed., 1995, 34, 2371.
T. Weskamp, W. C. Schattenmann, M. Spiegler, W. A.
Herrmann, Angew. Chem. Int. Ed., 1998, 37, 2490.
M. Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs,
Tetrahedron Lett., 1999, 40, 2247.
M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett., 1999, 1,
953.
J. Huang, E. D. Stevens, S. P Nolan, J. L Petersen, J. Am. Chem.
Soc., 1999, 121, 2674.
27 M. K. Denk, A. Tadani, K. Hatano, A. Lough, Angew. Chem.
Int. Ed. Engl., 1997, 36, 2607.
28 N. A. Giffin, A. D. Hendsbee, J. D. Masuda, Acta Cryst., 2010,
L. Ackermann, A. Fürstner, T. Weskamp, F. J. Kohl, W. A.
Herrmann, Tetrahedron Lett., 2001, 40, 4787.
10 For selected reviews on olefin metathesis see; a) G. C.
Vougioukalakis, R. H. Grubbs, Chem. Rev., 2010, 110, 1746.
b) C. Samojłowicz, M. Bieniek, and K. Grela, Chem. Rev.,
2009, 109, 3708. c) Olefin Metathesis: Theory and Practice
(Ed.: K. Grela), Wiley-VCH, Weinheim, 2014.; d) S. Kress, S.
Blechert, Chem. Soc. Rev., 2012, 41, 4389.
E
66, o2194.
29 B. Su, R. Ganguly, Y. Li, R. Kinjo, Angew. Chem. Int. Ed., 2014,
53, 13106.
30 There is a minor signal (ca. 2%) showing at 9.22 ppm in the
spectrum of 4c* taken at -40°C. This is probably a tiny
amount of starting material (4c) left in the mixture, although
11 K. Endo, R. H. Grubbs, J. Am. Chem. Soc., 2011, 133, 8525.
it might also be attributed to the syn-isomer of 4c*
.
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