Nickel-catalyzed cross-coupling reaction of allyl- and benzylzinc with alkenyl sulfides

Synlett

Volumn , Issue 13, 2008, Pages 2061-2063

  Baba, Yoko ^a   Toshimitsu, Akio ^a   Matsubara, Seijiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Allylation; Benzylation; Cross coupling; Nickel; Zinc

Indexed keywords

ALLYL COMPOUND; BENZYL DERIVATIVE; NICKEL; SULFIDE; ZINC;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; CROSS COUPLING REACTION; OXIDATION REDUCTION REACTION; STEREOCHEMISTRY;

EID: 49649105786     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1077960     Document Type: Article

References (22)

1. (a) Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
2. (b) Cross-Coupling Reactions: A Practical Guide, In Topics in Current Chemistry, Vol. 219; Miyaura, N., Ed.; Springer: Berlin, 2002.
3. (a) Ritter, K. Synthesis 1993, 735.
4. (b) Negishi, E.; Oweczarczyk, Z.; Swanson, D. R. Tetrahedron Lett. 1991, 32, 4453.
5. (c) Dunet, G.; Knochel, P. Synlett 2006, 407.
6. Lee, K.; Lee, J.; Lee, P. H. J. Org. Chem. 2002, 67, 8265.
7. Stille, J. K. Angew. Chem. Int. Ed Engl. 1986, 25, 508.
8. (a) Treatment of (E)-1-phenylthio-2-phenylethene (1a) with allylmagnesium bromide in the presence of nickel catalyst (the same reaction conditions as in entry 9 in Table 1) did not afford 3a.
9. (b) Treatment of (E)-1-bromo-2-phenylethene with allylzinc chloride in the presence of nickel catalyst (the same reaction conditions as in entry 9 in Table 1) gave 3a in 63% yield.
10. (a) Okamura, H.; Miura, M.; Takei, H. Tetrahedron Lett. 1979, 20, 43.
11. (b) Flandanese, V.; Marchese, G.; Mascolo, G.; Naso, F.; Ronzini, L. Tetrahedron Lett. 1988, 29, 3705.
12. (c) Itami, K.; Higashi, S.; Mineno, M.; Yoshida, J. Org. Lett. 2005, 7, 1219.
13. Takagi, K.; Hayama, N.; Sasaki, K. Bull. Chem. Soc. Jpn. 1984, 57, 1887.
14. Andersen, N. G.; Keay, B. A. Chem. Rev. 2001, 101, 997.
15. (a) Onaka, N.; Goto, T.; Mukaiyama, T. Tetrahedron Lett. 1979, 20, 1483.
16. (b) Quisenberry, K. T.; Smith, J. D.; Voehler, M.; Stec, D. F.; Hanusa, T. P.; Brennessel, W. W. J. Am. Chem. Soc. 2005, 127, 4376.
17. (a) Metzger, A.; Scade, A. A.; Knochel, P. Org. Lett. 2008, 10, 1107.
18. (b) Soorukram, D.; Boudet, N.; Malakhov, V.; Knochel, P. Synthesis 2007, 3915.
19. Ogawa, A.; Ikeda, T.; Kimura, K.; Hirao, T. J. Am. Chem. Soc. 1999, 121, 5108.
20. The use of Ni(0) catalyst which was prepared from Ni(II) and BuLi was not so effective. On the contrary Ni(II) catalyst gave the product with a reasonable yield. In this case, the formation of a radical species from benzylnickel intermediate may be a possible route. In fact, the addition of TEMPO interfered with the reaction. In the reaction of alkenyl sulfide with arylmethylzinc bromide (entry 4 in Table 3) addition of TEMPO (1 equiv) resulted in the low yield of 6a (14%).
21. 3): δ = 7.17-7.37 (m, 5 H), 6.42 (d, J = 15.9 Hz, 1 H), 6.23 (dt, J = 6.3, 15.9 Hz, 1 H), 5.90 (ddt, J = 6.3, 10.5, 15.9 Hz, 1 H), 5.05-5.16 (m, 2 H), 2.97 (ddt, J = 1.5, 6.3, 6.3 Hz, 2 H).
22. 3): δ = 7.17-7.38 (m, 10H), 6.46 (d, J = 15.9 Hz, 1 H), 6.36 (dt, J = 6.3, 15.9 Hz, 1 H), 3.55 (d, J = 6.3 Hz, 2 H).