Organometallics
Article
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D gs-HMBC experiments were recorded utilizing the standard
Althammer, A. Org. Lett. 2006, 8, 3457. (d) Huang, J.; Nolan, S. P.
J. Am. Chem. Soc. 1999, 121, 9889. (e) Ishikawa, S.; Manabe, K. Org.
Lett. 2007, 9, 5593. (f) Gauthier, D.; Beckendorf, S.; Gøgsig, T. M.;
Lindhardt, A. T.; Skrydstrup, T. J. Org. Chem. 2009, 74, 3536.
hmbcgpndqf pulse program. Spectral widths were 5100 and 45 300 Hz
for F2 and F1 dimensions, respectively, with 4096 points acquired in
the F2 domain. Acquisition was established in 512 F1 increments,
collecting 32 scans for each data point with 32 dummy scans before the
start of acquisition. The relaxation delay was set to 2 s. The refocusing
delay was optimized for long-range coupling: J(C−H)= 8 Hz. The raw
data obtained were zero filled to a 1024 × 1024 square matrix, and sine
multiplications with line broadening factors of 0.3 and 0.5 were applied in
F2 and F1 domains, respectively, prior to Fourier transformation.
(
g) Martin, R.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3844.
6) (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100,
009. (b) Tu, T.; Hou, X.-L.; Dai, L.-X. Org. Lett. 2003, 5, 3651.
(
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(c) Mariampillai, B.; Herse, C.; Lautens, M. Org. Lett. 2005, 7, 4745.
(d) Hansen, A. L.; Skrydstrup, T. J. Org. Chem. 2005, 70, 5997.
(e) Lautens, M.; Fang, Y.-Q. Org. Lett. 2003, 5, 3679. (f) Hartung,
̈
C. G.; Kohler, K.; Beller, M. Org. Lett. 1999, 1, 709. (g) Littke, A. F.;
ASSOCIATED CONTENT
Fu, G. C. J. Org. Chem. 1999, 64, 10. (h) Yang, C.; Lee, H. M.; Nolan,
S. P. Org. Lett. 2001, 3, 1511.
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*
S
Supporting Information
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(7) (a) Christensen, H.; Kiil, S.; Dam-Johansen, K.; Nielsen, O.;
Sommer, M. B. Org. Process Res. Dev. 2006, 10, 762. (b) Stauffer, S. R.;
Lee, S.; Stambuli, J. P.; Hauck, S. I.; Hartwig, J. F. Org. Lett. 2000, 2,
Figures and text giving the H NMR spectrum of freshly
prepared pure Pd (dba) and a detailed description of the
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3
experimental setup and synthetic procedure for the synthesis of
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423. (c) Grasa, G. A.; Viciu, M. S.; Huang, J.; Nolan, S. P. J. Org.
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Chem. 2001, 66, 7729. (d) Zhang, X.-X.; Buchwald, S. L. J. Org. Chem.
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000, 65, 8027. (e) Urgaonkar, S.; Verkade, J. G. J. Org. Chem. 2004,
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9, 9135.
AUTHOR INFORMATION
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(8) (a) Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2011, 111, 1596.
(b) Ananikov, V. P.; Khemchyan, L. L.; Beletskaya, I. P. Synlett 2009,
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375. (c) Ananikov, V. P.; Gayduk, K. A.; Beletskaya, I. P.; Khrustalev,
V. N.; Antipin, M. Yu. Eur. J. Inorg. Chem. 2009, 1149. (d) Ananikov,
V. P.; Orlov, N. V.; Beletskaya, I. P. Russ. Chem. Bull., Int. Ed. 2005, 54,
Notes
The authors declare no competing financial interest.
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76.
9) (a) Li, H.; Yang, M.; Qi, Y.; Xue, J. Eur. J. Org. Chem. 2011, 2662.
(b) Zhang, Z.; Zhang, Y.; Wang, J. ACS Catal. 2011, 1, 1621.
(10) (a) Soderberg, B. C. G.; Wallace, J. M.; Tamariz, J. Org. Lett.
002, 4, 1339. (b) Arcadi, A.; Cacchi, S.; Cascia, L.; Fabrizi, G.;
ACKNOWLEDGMENTS
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This work was supported by the Russian Foundation for Basic
Research (Project No. 10-03-00370), Grant MD-4969.2012.3,
and Programs of the Division of Chemistry and Material
Sciences of the RAS.
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Marinelli, F. Org. Lett. 2001, 3, 2501. (c) Larksarp, C.; Alper, H. J. Org.
Chem. 1999, 64, 4152.
(11) (a) Zhou, L.; Ye, F.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2010,
1
32, 13590. (b) Zhao, S.-C.; Shu, X.-Z.; Ji, K.-G.; Zhou, A.-X.; He, T.;
REFERENCES
■
Liu, X.-Y.; Liang, Y.-M. J. Org. Chem. 2011, 76, 1941. (c) Alper, H.;
Saldana-Maldonado, M. Organometallics 1989, 8, 1124. (d) Patil,
N. T.; Lutete, L. M.; Wu, H.; Pahadi, N. K.; Gridnev, I. D.; Yamamoto,
Y. J. Org. Chem. 2006, 71, 4270. (e) Awuah, E.; Capretta, A. Org. Lett.
(
1) (a) Vargas, V. C.; Rubio, R. J.; Hollis, T. K.; Salcido, M. E. Org.
Lett. 2003, 5, 4847. (b) Wade, J. V.; Krueger, C. A. J. Comb. Chem.
003, 5, 267. (c) Grasa, G. A.; Viciu, M. S.; Huang, J.; Zhang, C.;
Trudell, M. L.; Nolan, S. P. Organometallics 2002, 21, 2866. (d) Weng,
Z.; Teo, S.; Koh, L. L.; Hor, T. S. A. Organometallics 2004, 23, 4342.
e) Cai, C.; Chung, J. Y. L.; McWilliams, J. C.; Sun, Y.; Shultz, C. S.;
Palucki, M. Org. Process Res. Dev. 2007, 11, 328. (f) Bei, X.; Turner,
H. W.; Weinberg, W. H.; Guram, A. S.; Petersen, J. L. J. Org. Chem.
999, 64, 6797.
2) (a) Andrei, D.; Wnuk, S. F. J. Org. Chem. 2006, 71, 405. (b) Ross,
A. J.; Lang, H. L.; Jackson, R. F. W. J. Org. Chem. 2010, 75, 245.
c) Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 12527.
d) Goddard, C. M. L.; Massah, A. R.; Jackson, R. F. W. Tetrahedron
2
2
(
(
(
(
009, 11, 3210.
12) (a) Yang, F.-Y.; Cheng, C.-H. J. Am. Chem. Soc. 2001, 123, 761.
b) Wu, M.-Y.; Yang, F.-Y.; Cheng, C.-H. J. Org. Chem. 1999, 64, 2471.
c) Lofstedt, J; Franzen, J.; Backvall, J.-E. J. Org. Chem. 2001, 66, 8015.
d) Franzen, J.; Lofstedt, J; Dorange, I.; Backvall, J.-E. J. Am. Chem.
(
̈
́
̈
́
̈
̈
1
(
Soc. 2002, 124, 11246. (e) Toyofuki, M.; Murase, E.; Fujiwara, S.-i.;
Shin-ike, T.; Kuniyasu, H.; Kambe, N. Org. Lett. 2008, 10, 3957.
(
(
f) Xiao, W.-J.; Vasapollo, G.; Alper, H. J. Org. Chem. 1998, 63, 2609.
g) Chang, K.-J.; Rayabarapu, D. K.; Yang, F.-Y.; Cheng, C.-H. J. Am.
(
(
2
2
Chem. Soc. 2005, 127, 126.
13) (a) Geng, X.; Miller, M. L.; Lin, S.; Ojima, I. Org. Lett. 2003, 5,
733. (b) Turner, P. A.; Griffin, E. M.; Whatmore, J. L.; Shipman, M.
010, 66, 9175. (e) Luzung, M. R.; Patel, J. S.; Yin, J. J. Org. Chem.
010, 75, 8330. (f) Oswald, C. L.; Carillo-Marquez, T.; Caggiano, L.;
(
3
́
Jackson, R. F. W. Tetrahedron 2008, 64, 681.
3) (a) Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421.
b) Littke, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124,
343. (c) Garcıa-Cuadrado, D.; Cuadro, A. M.; Barchın, B. M.; Nunez,
A.; Caneque, T.; Alvarez-Builla, J.; Vaquero, J. J. J. Org. Chem. 2006,
1, 7989. (d) Su, W.; Urgaonkar, S.; McLaughlin, P. A.; Verkade, J. G.
Org. Lett. 2011, 13, 1056. (c) Severino, E. A.; Correia, C. R. D. Org.
Lett. 2000, 2, 3039. (d) Iimura, S.; Overman, L. E.; Paulini, R.;
Zakarian, A. J. Am. Chem. Soc. 2006, 128, 13095. (e) Trost, B. M.;
Thiel, O. R.; Tsui, H.-C. J. Am. Chem. Soc. 2003, 125, 13155.
(
(
6
́
́
̃
̃
(
f) Cuerva, J. M.; Gom
J. Org. Chem. 1997, 62, 7540.
14) (a) Mingos, D. M. P.; Vilar, R. J. Organomet. Chem. 1998, 557,
31. (b) Herbst, K.; Rink, B.; Dahlenburg, L.; Brorson, M.
Organometallics 2001, 20, 3655.
15) (a) Fuchita, Y.; Maruyama, H.; Kawatani, M.; Hiraki, K.
́ ́
ez-Bengoa, E.; Mendez, M.; Echavarren, A. M.
7
J. Am. Chem. Soc. 2004, 126, 16433. (e) Clapham, B.; Sutherland, A. J.
J. Org. Chem. 2001, 66, 9033.
4) (a) Raders, S. M.; Kingston, J. V.; Verkade, J. G. J. Org. Chem.
010, 75, 1744. (b) Itami, K.; Nokami, T.; Ishimura, Y.; Mitsudo, K.;
Kamei, T.; Yoshida, J-i. J. Am. Chem. Soc. 2001, 123, 11577.
(
1
(
2
(
(
(
c) Manoso, A. S.; DeShong, P. J. Org. Chem. 2001, 66, 7449.
d) Murata, M.; Watanabe, S.; Masuda, Y. Tetrahedron Lett. 1999, 40,
Polyhedron 1991, 10, 561. (b) Vicente, J.; Chicote, M. T.; Martínez-
Martínez, A. J.; Jones, P. G.; Bautista, D. Organometallics 2008, 27,
3254.
(16) (a) Vicente, J.; Abad, J.-A.; Fortsch, W.; Jones, P. G.; Fischer,
̈
A. K. Organometallics 2001, 20, 2704. (b) Getty, A. D.; Goldberg, K. I.
Organometallics 2001, 20, 2545.
9
255. (e) Denmark, S. E.; Baird, J. D. Org. Lett. 2004, 6, 3649.
f) Denamrk, S. E.; Wang, Z. Org. Lett. 2001, 3, 1073. (g) Montenegro,
J.; Bergueiro, J.; Saa, C.; Lopez, S. Org. Lett. 2009, 11, 141.
5) (a) Horibe, H.; Fukuda, Y.; Kondo, K.; Okuno, H.; Murakami, Y.;
(
́
́
(
Aoyama, T. Tetrahedron 2004, 60, 10701. (b) Yang, L.-M.; Huang,
(17) Ananikov, V. P.; Zalesskiy, S. S.; Kachala, V. V.; Beletskaya, I. P.
L.-F.; Luh, T.-Y. Org. Lett. 2004, 6, 1461. (c) Ackermann, L.;
J. Organomet. Chem. 2011, 696, 400.
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dx.doi.org/10.1021/om201217r | Organometallics 2012, 31, 2302−2309