Organic Letters
Letter
(8) (a) Gumrukcu, Y.; de Bruin, B.; Reek, J. N. H. Catalysts 2015, 5,
349−365. (b) Gumrukcu, Y.; de Bruin, B.; Reek, J. N. H. Chem. - Eur. J.
2014, 20, 10905−10909. (c) Gumrukcu, Y.; de Bruin, B.; Reek, J. N. H.
ChemSusChem 2014, 7, 890−896.
(9) (a) Gan, K.-H.; Jhong, C.-J.; Yang, S.-C. Tetrahedron 2008, 64,
1204−1212. (b) Yang, S.; Hsu, Y.; Gan, K. Tetrahedron 2006, 62, 3949−
3958. (c) Shue, Y.; Yang, S.; Lai, H. Tetrahedron Lett. 2003, 44, 1481−
1485.
(10) (a) Weaver, J. D.; Recio, A.; Grenning, A. J.; Tunge, J. A. Chem.
Rev. 2011, 111, 1846−1913. (b) Braun, M.; Meier, T. Angew. Chem., Int.
Ed. 2006, 45, 6952−6952. (c) Trost, B. M.; Fullerton, T. J. J. Am. Chem.
Soc. 1973, 95, 292−294. (d) Tsuji, J.; Takahashi, H.; Morikawa, A.
Tetrahedron Lett. 1965, 6, 4387−4388.
(11) (a) Lee, A.; Kim, H. J. Am. Chem. Soc. 2015, 137, 11250−11253.
(b) Lee, A.; Ahn, S.; Kang, K.; Kim, H.; Kim, W. Y. Org. Lett. 2014, 16,
5490−5493.
the rate-determining step and the rate is dependent on the
concentrations of the Pd catalyst, allyl alcohol, and acid additive.
Thus, Pd/briphos and pentafluorophenol significantly facilitate
the coupling reaction to provide N-allylated heterocycles under
mild conditions (30 °C) with high yields (71−99%).
ASSOCIATED CONTENT
* Supporting Information
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S
The Supporting Information is available free of charge on the
Experimental procedures and spectroscopic details (PDF)
AUTHOR INFORMATION
Corresponding Author
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(12) (a) Harusawa, S.; Yoneyama, H.; Usami, Y.; Yamamoto, D.; Zhao,
Z. Synthesis 2014, 46, 2815−2825. (b) Trost, B. M.; Crawley, M. L. Top.
Organomet. Chem. 2011, 38, 321−340. (c) Fahey, R. C. Annu. Rev.
Microbiol. 2001, 55, 333−356. (d) Kopple, J. D.; Swendseid, M. E. J.
Clin. Invest. 1975, 55, 881−891.
Notes
The authors declare no competing financial interest.
(13) (a) Kinoshita, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6,
4085−4088. (b) Wallner, O. A.; Szabo, K. J. J. Org. Chem. 2003, 68,
2934−2943. (c) Gagosz, F.; Zard, S. Z. Org. Lett. 2002, 4, 4345−4348.
(d) Kamijo, S.; Jin, T.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123,
9453−9454. (e) Baeckvall, J. E. Acc. Chem. Res. 1983, 16, 335−342.
(f) Trost, B. M. Acc. Chem. Res. 1980, 13, 385−393.
(14) In addition to the neutral π-allyl palladium complex, a cationic π-
allyl palladium complex can be proposed to explain the enhanced
reaction rate. (a) Manabe, K.; Kobayashi, S. Org. Lett. 2003, 5, 3241−
3244. (b) Amatore, C.; Jutand, A.; Meyer, G.; Mottier, L. Chem. - Eur. J.
1999, 5, 466−473.
ACKNOWLEDGMENTS
The authors are grateful for the financial supported provided by
the Institute of Basic Science (IBS-R004-D1).
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REFERENCES
■
(1) (a) Yang, Q.; Wang, Q.; Yu, Z. Chem. Soc. Rev. 2015, 44, 2305−
2329. (b) Butt, N. A.; Zhang, W. Chem. Soc. Rev. 2015, 44, 7929−7967.
(c) Kumar, R.; Van der Eycken, E. V. V Chem. Soc. Rev. 2013, 42, 1121−
1146. (d) Sundararaju, B.; Achard, M.; Bruneau, C. Chem. Soc. Rev. 2012,
41, 4467−4483. (e) Bandini, M.; Cera, G.; Chiarucci, M. Synthesis 2012,
44, 504−512.
(2) (a) Dhage, Y. D.; Shirai, R.; Arima, M.; Nakazima, A.; Hikawa, H.;
Kusakabe, I. A. T.; Takahashi, K.; Kato, K. RSC Adv. 2015, 5, 42623−
42627. (b) Yoshida, M.; Masaki, E.; Terumine, T.; Hara, S. Synthesis
2014, 46, 1367−1373. (c) Sawadjoon, S.; Sjoberg, P. J. R.; Orthaber, A.;
Matsson, O.; Samec, J. S. M. Chem. - Eur. J. 2014, 20, 1520−1524.
(d) Wang, Y.; Kang, Q. Org. Lett. 2014, 16, 4190−4193. (e) Lang, S. B.;
Locascio, T. M.; Tunge, J. A. Org. Lett. 2014, 16, 4308−4311.
(f) Larsson, J. M.; Szabo, K. J. J. Am. Chem. Soc. 2013, 135, 443−455.
(g) Lorion, M. M.; Gasperini, D.; Oble, J.; Poli, G. Org. Lett. 2013, 15,
3050−3053. (h) Tsupova, S.; Maeorg, U. Org. Lett. 2013, 15, 3381−
3383. (i) Li, Y.; Xuan, Q.; Liu, L.; Wang, D.; Chen, Y.; Li, C. J. Am. Chem.
Soc. 2013, 135, 12536−12539. (j) Chen, K.; Li, Y.; Pullarkat, S. A.;
Leung, P. Adv. Synth. Catal. 2012, 354, 83−87. (k) Hikawa, H.;
Yokoyama, Y. J. Org. Chem. 2011, 76, 8433−8439. (l) Hikawa, H.;
Yokoyama, Y. Org. Biomol. Chem. 2011, 9, 4044−4050. (m) Nishikata,
T.; Lipshutz, B. H. Org. Lett. 2009, 11, 2377−2379. (n) Muzart, J. Eur. J.
Org. Chem. 2007, 2007, 3077−3089. (o) Yokoyama, Y.; Takagi, N.;
Hikawa, H.; Kaneko, S.; Tsubaki, N.; Okuno, H. Adv. Synth. Catal. 2007,
349, 662−668.
(3) (a) Murakami, H.; Minami, T.; Ozawa, F. J. Org. Chem. 2004, 69,
4482−4486. (b) Ozawa, F.; Ishiyama, T.; Yamamoto, S.; Kawagishi, S.;
Murakami, H. Organometallics 2004, 23, 1698−1707. (c) Ozawa, F.;
Okamoto, H.; Kawagishi, S.; Yamamoto, S.; Minami, T.; Yoshifuji, M. J.
Am. Chem. Soc. 2002, 124, 10968−10969.
(4) (a) Trost, B. M.; Quancard, J. J. Am. Chem. Soc. 2006, 128, 6314−
6315. (b) Tamaru, Y. Eur. J. Org. Chem. 2005, 2005, 2647−2656.
(c) Kimura, M.; Futamata, M.; Mukai, R.; Tamaru, Y. J. Am. Chem. Soc.
2005, 127, 4592−4593.
(5) (a) Banerjee, D.; Jagadeesh, R. V.; Junge, K.; Junge, H.; Beller, M.
Angew. Chem., Int. Ed. 2012, 51, 11556−11560. (b) Banerjee, D.;
Jagadeesh, R. V.; Junge, K.; Junge, H.; Beller, M. ChemSusChem 2012, 5,
2039−2044.
(6) Ghosh, R.; Sarkar, A. J. Org. Chem. 2011, 76, 8508−8512.
(7) (a) Kayaki, Y.; Koda, T.; Ikariya, T. J. Org. Chem. 2004, 69, 2595−
2597. (b) Kayaki, Y.; Koda, T.; Ikariya, T. Eur. J. Org. Chem. 2004, 2004,
4989−4993.
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