Palladium-catalyzed γ-selective and stereospecific allyl-aryl coupling between acyclic allylic esters and arylboronic acids

Journal of the American Chemical Society

Volumn 132, Issue 2, 2010, Pages 879-889

  Ohmiya, Hirohisa ^a   Makida, Yusuke ^a   Li, Dong ^a   Tanabe, Masahito ^a   Sawamura, Masaya ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATIONS; ARYLBORONIC ACIDS; BENZYLIC; BIPYRIDINES; CHIRALITY TRANSFER; CINNAMYL ALCOHOLS; COUPLING PRODUCT; EFFICIENT SYNTHESIS; PALLADIUM CATALYST; PALLADIUM COMPLEXES; PHENANTHROLINES; SERTRALINE; STEREOGENIC CENTERS; STEREOSPECIFIC; STOICHIOMETRIC REACTION; SYNTHETIC UTILITY; TRANSMETALATION;

ACIDS; AROMATIC COMPOUNDS; CATALYSTS; DYES; ESTERS; FUNCTIONAL GROUPS; ORGANOMETALLICS; PALLADIUM; REACTION INTERMEDIATES; STEREOCHEMISTRY; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

PALLADIUM COMPOUNDS;

ACETIC ACID DERIVATIVE; ALKANE DERIVATIVE; ALLYLIC ACETATE DERIVATIVE; ANTIMONY; ARYLBORONIC ACID; BORONIC ACID DERIVATIVE; DIARLYALKANE DERIVATIVE; FLUORINE; PALLADIUM; PHENANTHROLINE; SILVER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; STEREOCHEMISTRY;

ALKANES; BORONIC ACIDS; CATALYSIS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PROPANOLS; SERTRALINE; STEREOISOMERISM;

EID: 74949133334     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9092264     Document Type: Article

References (71)

1. (a) Tsuji, J. Acc. Chem. Res. 1969, 2, 144-152.
2. (b) Trost, B. M. Tetrahedron 1977, 33, 2615-2649.
3. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422.
4. (d) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
5. Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, Germany, 2002.
6. Even for Cu-catalyzed systems, studies to date have focused largely on the reactions of primary allylic electrophiles that give terminal alkenes. For reviews of enantioselective allylic substitutions catalyzed by chiral copper complexes, see: (a) Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2005, 44, 4435-4439.
7. (b) Falciola, C. A.; Alexakis, A. Eur. J. Org. Chem. 2008, 3765-3780.
8. -. See: (a) Yoshikai, N.; Zhang, S.-L.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 12862-12863.
9. (b) Yamanaka, M.; Kato, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 6287-6293.
10. The reaction of MeCu(CN)Li and cis-1-D-5-methyl-2- cyclohexenyl acetate, which is a regiochemically unbiased substrate, showed 96:4 γ/α-selectivity: See ref 26b. For selected papers on γ-selective and stereoselective allylic substitution reactions with stoichiometric alkylcopper(I) reagents with excellent 1,3-chirality transfer, see: (a) Yanagisawa, A.; Nomura, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 1130-1136.
11. (b) Ibuka, T.; Akimoto, N.; Tanaka, M.; Nishii, S.; Yamamoto, Y. J. Org. Chem. 1989, 54, 4055-4061.
12. (c) Breit, B.; Demel, P.; Studte, C. Angew. Chem., Int. Ed. 2004, 43, 3786-3789.
13. (d) Leuser, H.; Perrone, S.; Liron, F.; Kneisel, F. F.; Knochel, P. Angew. Chem., Int. Ed. 2005, 44, 4627-4631.
14. When either arylcopper reagents or cinnamyl alcohol derivatives were employed, the γ-selectivity is considerably reduced. See: refs 5c and 29. For allylic substitution reactions with stoichiometric arylcopper(I) reagents with excellent γ-selectivity, see: (a) Harrington-Frost, N.; Leuser, H.; Calaza, M. I.; Kneisel, F. F.; Knochel, P. Org. Lett. 2003, 5, 2111-2114.
15. (b) Kiyotsuka, Y.; Acharya, H. P.; Katayama, Y.; Hyodo, T.; Kobayashi, Y. Org. Lett. 2008, 10, 1719-1722.
16. (c) Recently, Tomioka et al. reported the highly γ-selective, enantioselective substitution of cinnamyl bromides with aryl Grignard reagents. See: Selim, K. B.; Matsumoto, Y.; Yamada, K.; Tomioka, K. Angew. Chem., Int. Ed. 2009, 48, 8733-8735.
17. For Rh-catalyzed α-selective allylic substitutions with carbon nucleophiles, see: (a) Evans, P. A.; Nelson, J. D. Tetrahedron Lett. 1998, 39, 1725-1728.
18. (b) Evans, P. A.; Nelson, J. D. J. Am. Chem. Soc. 1998, 120, 5581-5582.
19. (c) Evans, P. A.; Leahy, D. K. J. Am. Chem. Soc. 2003, 125, 8974-8975.
20. (d) Evans, P. A.; Lawler, M. J. J. Am. Chem. Soc. 2004, 126, 8642-8643.
21. (e) Evans, P. A.; Uraguchi, D. J. Am. Chem. Soc. 2003, 125, 7158-7159.
22. (f) Ashfeld, B. L.; Miller, K. A.; Martin, S. F. Org. Lett. 2004, 6, 1321-1324. The stereospeci-ficity of the Rh catalysis has been explained based on the [σ+π] nature of the allyl (enyl) ligand.
23. For Ru-catalyzed α-selective allylic substitution with soft carbon nucleophiles, see: Kawatsura, M.; Ata, F.; Hayase, S.; Itoh, T. Chem. Commun. 2007, 4283-4285.
24. For Fe-catalyzed α-selective allylic substitutions with soft carbon nucleophiles, see: (a) Yanagisawa, A.; Nomura, N.; Yamamoto, H. Synlett 1991, 513-514.
25. (b) Plietker, B. Angew. Chem., Int. Ed. 2006, 45, 1469-1473.
26. (c) Plietker, B. Angew. Chem., Int. Ed. 2006, 45, 6053-6056.
27. For studies in this line [Cu-catalyzed γ-selective allylic and propargylic substitutions with bis(pinacolato)diboron], see: (a) Ito, H.; Kawakami, C.; Sawamura, M. J. Am. Chem. Soc. 2005, 127, 16034-16035.
28. (b) Ito, H.; Ito, S.; Sasaki, Y.; Matsuura, K.; Sawamura, M. J. Am. Chem. Soc. 2007, 129, 14856-14857.
29. (c) Ito, H.; Kosaka, Y.; Nonoyama, K.; Sasaki, Y.; Sawamura, M. Angew. Chem., Int. Ed. 2008, 47, 7424-7427.
30. (d) Ito, H.; Sasaki, Y.; Sawamura, M. J. Am. Chem. Soc. 2008, 130, 15774-15775.
31. 2, see:Moreno-Mañas, M.; Pérez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346-2351.
32. Part of this work was communicated. See: Ohmiya, H.; Makida, Y.; Tanaka, T.; Sawamura, M. J. Am. Chem. Soc. 2008, 130, 17276-17277.
33. Pd-catalyzed γ-selective allyl-aryl coupling between aryl iodides and allylic acetates has been reported. However, the reaction required harsh conditions (typically 180 °C) and was not stereoselective. See: (a) Mariamphillai, B.; Herse, C.; Lautens, M. Org. Lett. 2005, 7, 4745-4747.
34. Maddaford et al. reported the palladium-catalyzed C-glycosidation of peracetylated glycals (γ-substitution of γ-alkoxy-substituted allylic acetates with anti-stereochemistry) with arylboronic acids. This reaction goes through a (π-allyl)palladium(II) intermediate. Regioselectivity is controlled by the electronic effect of the oxygen functionality and is limited to this specific substrate class. See:Ramanauth, J.; Poulin, O.; Rakhit, S.; Maddaford, S. P. Org. Lett. 2001, 3, 2013-2015.
35. 2-carbon couplings between allyl alcohol derivatives and organoboron compounds via a (π-allyl) palladium(II) intermediate, see: (a) Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972-980.
36. (b) Legros, J.-Y.; Fiaud, J.-C. Tetrahedron Lett. 1990, 31, 7453-7456.
37. (c) Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384-3388.
38. (d) Kabalka, G. W.; Al-Masum, M. Org. Lett. 2006, 8, 11-13.
39. (e) Mino, T.; Kajiwara, K.; Shirae, Y.; Sakamoto, M.; Fujita, T. Synlett 2008, 2711-2715.
40. (f) Nishikata, T.; Lipshutz, B. H. J. Am. Chem. Soc. 2009, 131, 12103-12105. See also ref 14.
41. For rhodium-catalyzed allyl-aryl couplings between cis-4- cyclopenten-1,3-diol derivatives and arylboron compounds that afforded trans-2-aryl-3-cyclopenten-1-ol derivatives, see: (a) Menard, F.; Chapman, T. M.; Dockendorff, C.; Lautens, M. Org. Lett. 2006, 8, 4569-4572.
42. (b) Miura, T.; Takahashi, Y.; Murakami, M. Chem. Commun. 2007, 595-597.
43. For palladium-catalyzed oxidative Mizoroki-Heck-type reactions of allylic acetates with arylboronic acids, see: (a) Delcamp, J. H.; White, M. C. J. Am. Chem. Soc. 2006, 128, 15076-15077.
44. (b) Ruan, J.; Li, X.; Saidi, O.; Xiao, J. J. Am. Chem. Soc. 2008, 130, 2424-2425.
45. (c) Su, Y.; Jiao, N. Org. Lett. 2009, 11, 2980-2983.
46. For γ-selective allylic substitution reactions with stoichiometric arylcopper(I) reagents with excellent 1,3-chirality transfer, see: refs 6a and 6b.
47. 1H NMR and GC analysis of the crude product, using the corresponding α-isomer (3f) as a reference compound.
48. (a) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Angew. Chem., Int. Ed. 2003, 42, 2768-2770.
49. (b) Yamamoto, Y.; Nishikata, T.; Miyaura, N. Pure Appl. Chem. 2008, 80, 807-817.
50. (c) Davis, J. A.; Hartley, F. R.; Muray, S. G. J. Chem. Soc., Dalton Trans. 1980, 2246-2249.
51. Reducing the amount of phenylboronic acid (2a) decreased the yield of the coupling product 3a under otherwise identical conditions.
52. For Schemes 2 and 3 and Tables 2 and 3, the crude materials after removal of the catalyst and boron compounds consisted of the coupling product, biaryl, unreacted allylic acetate, and/or unidentified compounds. The Mizoroki-Heck-type product was not detected. The isolated products were contaminated with traces of unidentified materials (0.1-5%). The isolated yields for the reaction of 1g,h,i,l in Tables 2 and 3 may be reduced by the evaporation of the products.
53. The reaction of terminal alkenes 1d and 1i were carried out with THF solvent (Table 2, entries 9 and 14). The use of THF suppressed the formation of unidentified side products.
54. 6,10 mol %; THF; 60 °C] afforded the corresponding coupling product in only 17% yield.
55. See ref 6c and references therein.
56. (a) Goering, H. L.; Seitz, E. P.; Tseng, C. C. J. Org. Chem. 1981, 46, 5304-5308.
57. (b) Goering, H. L.; Kantner, S. S. J. Org. Chem. 1984, 49, 422-426.
58. Goering, H. L.; Tseng, C. C. J. Org. Chem. 1983, 48, 3986-3990. See also ref 26b.
59. (a) Goering, H. L.; Kantner, S. S.; Tseng, C. C. J. Org. Chem. 1983, 48, 715-721. For related work, see also:
60. (b) Goering, H. L.; Kantner, S. S. J. Org. Chem. 1981, 46, 2144-2148.
61. (c) Goering, H. L.; Kantner, S. S. J. Org. Chem. 1985, 50, 1597-1599.
62. Alexakis, A.; Hajjaji, S. E.; Polet, D.; Rathgeb, X. Org. Lett. 2007, 9, 3393-3395.
63. For syntheses of (+)-sertraline, see: (a) Quallich, G. J. Chirality 2005, 17, S120-S126.
64. (b) Corey, E. J.; Gant, T. G. Tetrahedron Lett. 1994, 35, 5373-5376.
65. (c) Lautens, M.; Rovis, T. J. Org. Chem. 1997, 62, 5246-5247.
66. (d) Davies, H. M. L.; Stafford, D. G.; Hansen, T. Org. Lett. 1999, 1, 233-236. See also refs 6c and 29.
67. Enders, D.; Bartsch, M.; Backhaus, D. Synlett 1995, 869-870.
68. De Felice, V.; de Renzi, A.; Fraldi, N.; Panunzi, B. Inorg. Chim. Acta 2009, 362, 2015-2019.
69. 13C NMR measurement was unsuccessful.
70. This is contradictory with the reported results of the oxidative Mizoroki-Heck-type arylation of allylic esters with arylboronic acids. See ref 17.
71. For Mizoroki-Heck-type arylation of allylic acetates with aryl iodides, see: (a) Pan, D.; Chen, A.; Su, Y.; Zhou, W.; Li, S.; Jia, W.; Xiao, J.; Liu, Q.; Zhang, L.; Jiao, N. Angew. Chem., Int. Ed. 2008, 47, 4729-4732.