N. Nishioka, T. Koizumi / Tetrahedron Letters 52 (2011) 3662–3665
3665
Org. Lett. 2000, 2, 527; (f) Labrosse, J.-R.; Lhoste, P.; Sinou, D. Tetrahedron Lett.
1999, 40, 9025; (g) Labrosse, J.-R.; Lhoste, P.; Delbecop, F.; Sinou, D. Eur. J. Org.
Chem. 2003, 2813.
was obtained in 61% yield as expected. On the other hand, allylic
amine 4ab prepared in situ did not afford 9. Allylic amine 4ab
was only isolated (81%) as shown in Scheme 4(2). Thus, we found
that the intermediate product 7k could react with 3b, whereas
the reaction of allylic amine 4ab with BnOH did not proceed.
In conclusion, we have developed the Pd(0)-catalyzed reaction
of propargyl carbonate 1 with phenols and nucleophiles for the
synthesis of multi-functional allylic compounds. The reactions
proceeded in regio and chemoselective manners, and various
substituted allylic compounds could be synthesized. A variety of
nucleophiles such as secondary amines, phthalimide and carbon
nucleophiles gave 2-aryloxyallylic compounds in good to excel-
lent yields. On the other hand, the reaction with aliphatic alcohols
exhibited different chemoselectivity and afforded 2-alkoxyallyl
aryl ethers.
4. (a) Yoshida, M.; Higuchi, M.; Shishido, K. Tetrahedron Lett. 2008, 49, 1678; (b)
Yoshida, M.; Morishita, Y.; Fujita, M.; Ihara, M. Tetrahedron Lett. 2004, 45, 1861;
(c) Yoshida, M.; Morishita, Y.; Fujita, M.; Ihara, M. Tetrahedron 2005, 61, 4381;
(d) Yoshida, M.; Higuchi, M.; Shishido, K. Tetrahedron 2010, 66, 2675.
5. For recent examples of palladium-catalyzed cyclization of propargylic
compounds with nucleophiles, see: (a) Kozawa, Y.; Mori, M. Tetrahedron Lett.
2001, 42, 4869; (b) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 1499; (c)
Kozawa, Y.; Mori, M. J. Org. Chem. 2003, 68, 8068; (d) Ambrogio, I.; Cacchi, S.;
Fabrizi, G. Org. Lett. 2006, 8, 2083; (e) Duan, X.-H.; Guo, L.-N.; Bi, H.-P.; Liu, X.-
Y.; Liang, Y.-M. Org. Lett. 2006, 8, 5777; (f) Guo, L.-N.; Duan, X.-H.; Bi, H.-P.; Liu,
X.-Y.; Liang, Y.-M. J. Org. Chem. 2007, 72, 1538; (g) Bi, H.-P.; Liu, X.-Y.; Gou, F.-
R.; Guo, L.-N.; Duan, X.-H.; Liang, Y.-M. Org. Lett. 2007, 9, 3527; (h) Bi, H.-P.; Liu,
X.-Y.; Gou, F.-R.; Guo, L.-N.; Duan, X.-H.; Shu, X.-Z.; Liang, Y.-M. Angew. Chem.,
Int. Ed. 2007, 46, 7068; (i) Guo, L.-N.; Duan, X.-H.; Liang, Y.-M. Acc. Chem. Res.
2011, 44, 111; (j) Ohno, H.; Okano, A.; Kosaka, S.; Tsukamoto, K.; Ohata, M.;
Ishihara, K.; Maeda, H.; Tanaka, T.; Fujii, N. Org. Lett. 2008, 10, 1171; (k) Inuki,
S.; Yoshimitsu, Y.; Oishi, S.; Fujii, N.; Ohno, H. J. Org. Chem. 2010, 75, 3831; (l) Bi,
H.-P.; Guo, L.-N.; Gou, F.-R.; Duan, X.-H.; Liu, X.-Y.; Liang, Y.-M. J. Org. Chem.
2008, 73, 4713; (m) Yoshida, M.; Higuchi, M.; Shishido, K. Org. Lett. 2009, 11,
4752; (n) Yoshida, M.; Komatsuzaki, Y.; Nemoto, H.; Ihara, M. Org. Biomol.
Chem. 2004, 2, 3099.
Supplementary data
Supplementary data associated with this article can be found, in
6. For recent examples of palladium-catalyzed intermolecular reaction of
propargylic compounds with two nucleophiles, see: (a) Koizumi, T.; Sugie, K.;
Kiyonaga, O.; Yamanaka, M.; Kawabata, S. Macromolecules 2004, 37, 9670; (b)
Takemura, T.; Sugie, K.; Nishino, H.; Kawabata, S.; Koizumi, T. J. Polym. Sci., Part
A: Polym. Chem. 2008, 46, 2250; (c) Nishioka, N.; Koizumi, T. J. Polym. Sci., Part A:
Polym. Chem. 2011, 49, 642; (d) Nishioka, N.; Koizumi, T. Eur. Polymer J. 2011,
47, 1142.
7. (a) Organ, M. G.; Arvanitis, E. A.; Dixon, C. E.; Cooper, J. T. J. Am. Chem. Soc. 2002,
124, 1288; (b) Organ, M. G.; Miller, M.; Konstantinou, Z. J. Am. Chem. Soc. 1998,
120, 9283.
8. (a) Bukovec, C.; Kazmaier, U. Org. Lett. 2009, 11, 3518; (b) Kazmaier, U.; Schauß,
D.; Raddatz, S.; Pohlman, M. Chem. Eur. J. 2001, 7, 456.
9. DPPE = 1,2-bis(diphenylphosphino)ethane.
10. DPPP = 1,3-bis(diphenylphosphino)propane.
11. DPPB = 1,4-bis(diphenylphosphino)butane.
References and notes
1. Tsuji, J. Palladium Reagents and Catalysts, New Perspectives for the 21st Century;
Willey: UK, Chichester, 2004. p 431.
2. (a) Tsuji, J.; Watanabe, H.; Minami, I.; Shimizu, I. J. Am. Chem. Soc. 1985, 107,
2196; (b) Minami, I.; Yuhara, M.; Watanabe, H.; Tsuji, J. J. Organomet. Chem.
1987, 334, 225; (c) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34,
2589; (d) Casey, C. P.; Nash, J. R.; Yi, C. S.; Selmeczy, A. D.; Chung, S.; Powell, D.
R.; Hayashi, R. K. J. Am. Chem. Soc. 1998, 120, 722.
3. (a) Dominczak, N.; Lhoste, P.; Kryczka, B.; Sinou, D. J. Mol. Catal. A: Chem. 2007,
264, 110; (b) Dominczak, N.; Damez, C.; Rhers, B.; Labrosse, J.; Lhoste, P.;
Kryczka, B.; Sinou, D. Tetrahedron 2005, 61, 2589; (c) Damez, C.; Labrosse, J.-R.;
Lhoste, P.; Sinou, D. Tetrahedron Lett. 2003, 44, 557; (d) Labrosse, J.-R.; Lhoste,
P.; Sinou, D. J. Org. Chem. 2001, 66, 6634; (e) Labrosse, J.-R.; Lhoste, P.; Sinou, D.
12. DPEphos = bis[(2-diphenylphosphino)phenyl]ether, Kranenburg, M.; van der
Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K.; Fraanje, J.
Organometallics 1995, 14, 3081.