Precatalyst for Primary Alkylamine C–N Cross-Coupling Reactions
plied to the single point energies using the DFT-D3 program.[33]
Data provided in this paper are the enthalpy changes of ligand
dissociation, while free energy changes for these processes are pro-
vided in the supplementary information. This level of theory was
chosen as it has been shown to be successful in modelling similar
systems recently.[6a] All quantum-chemical calculations were under-
taken using the Gaussian 09 program suite.[34]
[7]
[8]
a) S. Ge, J. F. Hartwig, Angew. Chem. Int. Ed. 2012, 51, 12837–
12841; Angew. Chem. 2012, 124, 13009; b) J. Yamaguchi, K.
Muto, K. Itami, Eur. J. Org. Chem. 2013, 19–30.
a) J. Yi, X. Lu, Y.-Y. Sun, B. Xiao, L. Liu, Angew. Chem. Int.
Ed. 2013, 52, 12409–12413; Angew. Chem. 2013, 125, 12635; b)
I. P. Beletskaya, G. V. Latyshev, A. V. Tsvetkov, N. V. Lukashev,
Tetrahedron Lett. 2003, 44, 5011–5013; c) D. Gallego, A.
Brück, E. Irran, F. Meier, M. Kaupp, M. Driess, J. F. Hartwig,
J. Am. Chem. Soc. 2013, 135, 15617–15626.
a) D. K. Nielsen, A. G. Doyle, Angew. Chem. Int. Ed. 2011,
50, 6056–6059; Angew. Chem. 2011, 123, 6180; b) K. Muto, J.
Yamaguchi, A. Lei, K. Itami, J. Am. Chem. Soc. 2013, 135,
16384–16387; c) K. Amaike, K. Muto, J. Yamaguchi, K. Itami,
J. Am. Chem. Soc. 2012, 134, 13573–13576.
a) R. Omar-Amrani, A. Thomas, E. Brenner, R. Schneider, Y.
Fort, Org. Lett. 2003, 5, 2311–2314; b) S. D. Ramgren, A. L.
Silberstein, Y. Yang, N. K. Garg, Angew. Chem. Int. Ed. 2011,
50, 2171–2173; Angew. Chem. 2011, 123, 2219; c) C. Desmarets,
R. Schneider, Y. Fort, J. Org. Chem. 2002, 67, 3029–3036; d)
T. Mesganaw, A. L. Silberstein, S. D. Ramgren, N. F. F. Nathel,
X. Hong, P. Liu, N. K. Garg, Chem. Sci. 2011, 2, 1766–1771.
CCDC-1045787 contains the supplementary crystallographic data
for this paper. These data can be obtained free of charge from The
Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/
data_request/cif.
[9]
Supporting Information (see footnote on the first page of this arti-
cle): Full experimental details, NMR spectra, computational data
and procedures for kinetic experiments can be found in the Sup-
porting Information.
[10]
Acknowledgments
[11]
[12]
a) C. Bolm, J. P. Hildebrand, J. Rudolph, Synthesis 2000, 911–
913; b) B. Saito, G. C. Fu, J. Am. Chem. Soc. 2008, 130, 6694–
6695; c) S. Ge, J. F. Hartwig, J. Am. Chem. Soc. 2011, 133,
16330–16333.
The authors would like to thank Associate Professor Lindsay Byrne
at UWA for NMR assistance. Prof. Reto Dorta is gratefully ac-
knowledged for helpful mechanistic discussions. The authors are
indebted to the Danish National Research Foundation, Centre for
Materials Crystallography for financial support (grant number
DNRF93). S. S. K. appreciates support by The University of
Western Australia (PhD scholarship, UWA SIRF/UIS). The au-
thors acknowledge the facilities and the scientific and technical as-
sistance of the Australian Microscopy & Microanalysis Research
Facility at the Centre for Microscopy, Characterization & Analysis,
The University of Western Australia, a facility funded by the Uni-
versity, State and Commonwealth Governments.
a) E. Brenner, Y. Fort, Tetrahedron Lett. 1998, 39, 5359–5362;
b) B. C. Hamann, J. F. Hartwig, J. Am. Chem. Soc. 1998, 120,
3694–3703; c) S. S. Kampmann, A. N. Sobolev, G. A. Koutsan-
tonis, S. G. Stewart, Adv. Synth. Catal. 2014, 356, 1967–1973;
d) M. Yamashita, J. V. Cuevas Vicario, J. F. Hartwig, J. Am.
Chem. Soc. 2003, 125, 16347–16360; e) C.-Y. Gao, X. Cao, L.-
M. Yang, Org. Biomol. Chem. 2009, 7, 3922–3925; f) M. J. Igle-
sias, J. F. Blandez, M. R. Fructos, A. Prieto, E. Álvarez, T. R.
Belderrain, M. C. Nicasio, Organometallics 2012, 31, 6312–
6316; g) A. R. Martin, Y. Makida, S. Meiries, A. M. Z. Slawin,
S. P. Nolan, Organometallics 2013, 32, 6265–6270; h) J. P.
Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 6054–
6058; i) E. Brenner, R. Schneider, Y. Fort, Tetrahedron 1999,
55, 12829–12842; j) Chen, L.-M. Yang, J. Org. Chem. 2007, 72,
6324–6327; k) C.-Y. Gao, L.-M. Yang, J. Org. Chem. 2008, 73,
1624–1627; l) G. Manolikakes, A. Gavryushin, P. Knochel, J.
Org. Chem. 2008, 73, 1429–1434; m) M. J. Iglesias, A. Prieto,
M. C. Nicasio, Adv. Synth. Catal. 2010, 352, 1949–1954; n) X.-
H. Fan, G. Li, L.-M. Yang, J. Organomet. Chem. 2011, 696,
2482–2484.
N. H. Park, G. Teverovskiy, S. L. Buchwald, Org. Lett. 2014,
16, 220–223.
S. Ge, R. A. Green, J. F. Hartwig, J. Am. Chem. Soc. 2014, 136,
1617–1627.
a) N. F. Fine Nathel, J. Kim, L. Hie, X. Jiang, N. K. Garg,
ACS Catal. 2014, 4, 3289–3293; b) L. Hie, S. D. Ramgren, T.
Mesganaw, N. K. Garg, Org. Lett. 2012, 14, 4182–4185.
A. R. Martin, D. J. Nelson, S. Meiries, A. M. Z. Slawin, S. P.
Nolan, Eur. J. Org. Chem. 2014, 3127–3131.
[1] a) S. Brase, A. de Meijere, Metal-Catalyzed Cross-Coupling Re-
actions, Wiley-VCH, Weinheim, Germany, 2008; b) E.-i. Negi-
shi, in: Handbook of Organopalladium Chemistry for Organic
Synthesis John Wiley & Sons, USA, 2003, p. 1–15; c) D. Stein-
born, Fundamentals of Organometallic Catalysis, Wiley-VCH,
Weinheim, Germany, 2011; d) J. F. Hartwig, Organotransition
Metal Chemistry, From Bonding to Catalysis, University Sci-
ence Books, 2010; e) S. A. Janine Cossy, in: Modern Tools for
the Synthesis of Complex Bioactive Molecules, John Wiley &
Sons, Hoboken, New Jersey, 2012, p. 1–32.
[2] a) Y. Tamaru, Modern Organonickel Chemistry, Wiley-VCH,
Weinheim, Germany, 2005; b) S. Z. Tasker, E. A. Standley, T. F.
Jamison, Nature 2014, 509, 299–309.
[3] a) Lin, L. Liu, Y. Fu, S.-W. Luo, Q. Chen, Q.-X. Guo, Organo-
metallics 2004, 23, 2114–2123; b) T. T. Tsou, J. K. Kochi, J.
Am. Chem. Soc. 1979, 101, 6319–6332.
[4] a) B. M. Rosen, K. W. Quasdorf, D. A. Wilson, N. Zhang,
A. M. Resmerita, N. K. Garg, V. Percec, Chem. Rev. 2011, 111,
1346–1416; b) A. J. Oelke, J. Sun, G. C. Fu, J. Am. Chem. Soc.
2012, 134, 2966–2969; c) A. R. Ehle, Q. Zhou, M. P. Watson,
Org. Lett. 2012, 14, 1202–1205; d) J. J. Garcia, N. M. Brunkan,
W. D. Jones, J. Am. Chem. Soc. 2002, 124, 9547–9555; e) T.
Shimasaki, M. Tobisu, N. Chatani, Angew. Chem. Int. Ed.
2010, 49, 2929–2932; Angew. Chem. 2010, 122, 2991; f) P.
Leowanawat, N. Zhang, V. Percec, J. Org. Chem. 2012, 77,
1018–1025.
[13]
[14]
[15]
[16]
[17]
a) A. Borzenko, N. L. Rotta-Loria, P. M. MacQueen, C. M.
Lavoie, R. McDonald, M. Stradiotto, Angew. Chem. Int. Ed.
2015, 54, 3773–3777; Angew. Chem. 2015, 127, 3844; b) R. A.
Green, J. F. Hartwig, Angew. Chem. Int. Ed. 2015, 54, 3768–
3772; Angew. Chem. 2015, 127, 3839.
S. Iyer, C. Ramesh, A. Ramani, Tetrahedron Lett. 1997, 38,
8533–8536.
[18]
[19]
[20]
Y. Yatsumonji, Y. Ishida, A. Tsubouchi, T. Takeda, Org. Lett.
2007, 9, 4603–4606.
[5] L. Ilies, T. Matsubara, E. Nakamura, Org. Lett. 2012, 14,
5570–5573.
a) C. A. Tolman, W. C. Seidel, J. D. Druliner, P. J. Domaille,
Organometallics 1984, 3, 33–38; b) S. Arai, Y. Amako, X. Yang,
A. Nishida, Angew. Chem. Int. Ed. 2013, 52, 8147–8150; An-
gew. Chem. 2013, 125, 8305; c) A. Falk, A.-L. Göderz, H.-G.
Schmalz, Angew. Chem. Int. Ed. 2013, 52, 1576–1580; Angew.
Chem. 2013, 125, 1617.
[6] a) T. M. Gøgsig, J. Kleimark, S. O. Nilsson Lill, S. Korsager,
A. T. Lindhardt, P.-O. Norrby, T. Skrydstrup, J. Am. Chem.
Soc. 2012, 134, 443–452; b) S. Z. Tasker, A. C. Gutierrez, T. F.
Jamison, Angew. Chem. Int. Ed. 2014, 53, 1858–1861; Angew.
Chem. 2014, 126, 1889.
Eur. J. Org. Chem. 2015, 5995–6004
© 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
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