Organic Letters
Letter
arylation, alkylation, and vinylation of a wide range of aryl,
heteroaryl, alkyl halides, and pseudohalides with different
organoboronate reagents using the Suzuki−Miyaura coupling.
In most cases, high yields of isolated products are obtained.
Deprotonated neutral Ni(II) complexes seem to be key
intermediates in the catalytic reaction. In one case, it has
been exemplarily shown that such a species is indeed an active
catalyst.
Fu, G. C. J. Am. Chem. Soc. 2013, 135, 624−627. (h) Ramgren, S. D.;
Hie, L.; Ye, Y.; Garg, N. K. Org. Lett. 2013, 15, 3950−3953.
(
10) (a) Tobisu, M.; Shimasaki, T.; Chatani, N. Angew. Chem., Int. Ed.
2
2
008, 47, 4866−4869. (b) Tobisu, M.; Chatani, N. Acc. Chem. Res.
015, 48, 1717−1726. (c) Cornella, J.; Zarate, C.; Martin, R. Chem.
Soc. Rev. 2014, 43, 8081−8097.
(
11) (a) Quasdorf, K. W.; Riener, M.; Petrova, K. V.; Garg, N. K. J.
Am. Chem. Soc. 2009, 131, 17748−17749. (b) Antoft-Finch, A.;
Blackburn, T.; Snieckus, V. J. Am. Chem. Soc. 2009, 131, 17750−
1
7752. (c) Xu, L.; Li, B. J.; Wu, Z. H.; Guan, B. T.; Wang, B. Q.; Zhao,
ASSOCIATED CONTENT
K. Q.; Shi, Z. J. Org. Lett. 2010, 12, 884−887. (d) Huang, K.; Li, G.;
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Huang, W. P.; Yu, D. G.; Shi, Z. J. Chem. Commun. 2011, 47, 7224−
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S
Supporting Information
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226. (e) Quasdorf, K. W.; Antoft-Finch, A.; Liu, P.; Silberstein, A. L.;
Komaromi, A.; Blackburn, T.; Ramgren, S. D.; Houk, K. N.; Snieckus,
V.; Garg, N. K. J. Am. Chem. Soc. 2011, 133, 6352−6363.
(f) Baghbanzadeh, M.; Pilger, C.; Kappe, C. O. J. Org. Chem. 2011,
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6, 1507−1510. (g) Ke, H.; Chen, X.; Zou, G. J. Org. Chem. 2014, 79,
Crystallographic data 3 and 6 (CCDC entries 1472541
132−7140. (h) Xing, C.-H.; Lee, J.-R.; Tang, Z.-Y.; Zheng, J. R.; Hu,
(
3) and 1472542 (6)) (CIF)
Q.-S. Adv. Synth. Catal. 2011, 353, 2051−2059.
Complete crystallographic data, synthetic procedures,
(12) (a) Guan, B.-T.; Wang, Y.; Li, B.-J.; Yu, D.-G.; Shi, Z.-J. J. Am.
Chem. Soc. 2008, 130, 14468−14470. (b) Quasdorf, K. W.; Tian, X.;
Garg, N. K. J. Am. Chem. Soc. 2008, 130, 14422−14423.
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13
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H, C{ H}, and P{ H} NMR spectra of all complexes
and organic products (PDF)
(13) (a) Quasdorf, K. W.; Tian, X.; Garg, N. K. J. Am. Chem. Soc.
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008, 130, 14422−14423. (b) Guan, B.-T.; Wang, Y.; Li, B.-J.; Yu, D.-
AUTHOR INFORMATION
G.; Shi, Z.-J. J. Am. Chem. Soc. 2008, 130, 14468−14470. (c) Li, Z.;
Zhang, S.-L.; Fu, Y.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2009, 131,
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*
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815−8823. (d) Li, B.-J.; Li, Y.-Z.; Lu, X.-Y.; Liu, J.; Guan, B.-T.; Shi,
Z.-J. Angew. Chem., Int. Ed. 2008, 47, 10124−10127. (e) Shimasaki, T.;
Tobisu, M.; Chatani, N. Angew. Chem., Int. Ed. 2010, 49, 2929−2932.
Notes
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f) Molander, G. A.; Beaumard, F. Org. Lett. 2010, 12, 4022−4025.
The authors declare no competing financial interest.
(
14) Weires, N. A.; Baker, E. L.; Garg, N. K. Nat. Chem. 2015, 8, 75−
9.
(15) (a) Tang, Z. Y.; Hu, Q. S. J. Am. Chem. Soc. 2004, 126, 3058.
b) Brun, S.; Pla-Quintana, A.; Roglans, A.; Porschke, K.-R.; Goddard,
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ACKNOWLEDGMENTS
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(
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M.M. and K.K. gratefully acknowledge the financial support by
the Austrian Science Fund (FWF) (Project No. P28866-N34).
The X-ray center of the Vienna University of Technology is
acknowledged for financial support and for providing access to
the single-crystal diffractometer.
R. Organometallics 2012, 31, 1983−1990. (c) Zell, T.; Feierabend, M.;
Halfter, B.; Radius, U. J. Organomet. Chem. 2011, 696, 1380−1387.
(d) Zell, T.; Fischer, P.; Schmidt, D.; Radius, U. Organometallics 2012,
31, 5065−5073. (e) Oertel, A. M.; Ritleng, V.; Chetcuti, M. J.
Organometallics 2012, 31, 2829−2840.
(
1
16) (a) Ro
37, 7998−8001. (b) Ro
Angew. Chem., Int. Ed. 2015, 54, 15046−15050.
17) (a) Kuroda, J. i.; Inamoto, K.; Hiroya, K.; Doi, T. Eur. J. Org.
Chem. 2009, 2009, 2251−2261. (b) Tu, T.; Mao, H.; Herbert, C.; Xu,
M.; Dotz, K. H. Chem. Commun. 2010, 46, 7796−7798. (c) Xu, M.; Li,
X.; Sun, Z.; Tu, T. Chem. Commun. 2013, 49, 11539−11541.
18) Benito-Garagorri, D.; Becker, E.; Wiedermann, J.; Lackner, W.;
Pollak, M.; Mereiter, K.; Kisala, J.; Kirchner, K. Organometallics 2006,
5, 1900−1913.
̈
sler, S.; Obenauf, J.; Kempe, R. J. Am. Chem. Soc. 2015,
̈
sler, S.; Ertl, M.; Irrgang, T.; Kempe, R.
REFERENCES
■
(
3
1) Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 20,
(
437−3440.
(
(
2) Miyaura, N. Top. Curr. Chem. 2002, 219, 11−59.
̈
3) Tsuji, J. Palladium Reagents and Catalysis, 2nd ed.; Wiley: West
Sussex, U.K., 2004.
4) De Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling
Reactions, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2004.
(
(
2
(
(
5) Han, F. S. Chem. Soc. Rev. 2013, 42, 5270−5298.
6) Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509,
2
(
(
99−309.
7) Maluenda, I.; Navarro, O. Molecules 2015, 20, 7528−7557.
8) (a) Inamoto, K.; Kuroda, J.; Hiroya, K.; Noda, Y.; Watanabe, M.;
Sakamoto, T. Organometallics 2006, 25, 3095−3098. (b) Martin, A. R.;
Makida, Y.; Meiries, S.; Slawin, A. M. Z.; Nolan, S. P. Organometallics
2
013, 32, 6265−6270. (c) Wei, Y.; Petronilho, A.; Mueller-Bunz, H.;
Albrecht, M. Organometallics 2014, 33, 5834−5844. (d) Bernhammer,
J. C.; Huynh, H. V. Organometallics 2014, 33, 5845−5851. (e) Li, H.;
Zhong, Y.-L.; Chen, C.; Ferraro, A. E.; Wang, D. Org. Lett. 2015, 17,
3
3
9
616−3619. (f) Magano, J.; Monfette, S. ACS Catal. 2015, 5, 3120−
123. (g) Molander, G. A.; Brown, A. R. J. Org. Chem. 2006, 71,
681−9686.
(
9) (a) Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 1340−1341.
(
b) Tobisu, M.; Xu, T.; Shimasaki, T.; Chatani, N. J. Am. Chem. Soc.
2
011, 133, 19505−19511. (c) Ge, S.; Hartwig, J. F. Angew. Chem., Int.
Ed. 2012, 51, 12837−12841. (d) Zhang, X.; Yang, C. Adv. Synth. Catal.
2
2
015, 357, 2721−2727. (e) Di Franco, T.; Boutin, N.; Hu, X. Synthesis
013, 45, 2949−2958. (f) Wilsily, A.; Tramutola, F.; Owston, N. A.;
Fu, G. C. J. Am. Chem. Soc. 2012, 134, 5794−5797. (g) Zultanski, S. L.;
D
Org. Lett. XXXX, XXX, XXX−XXX