Chelation-Controlled Mizoroki-Heck Reactions

The Mizoroki-Heck Reaction

Volumn , Issue , 2009, Pages 259-279

  Itami, Kenichiro ^a   Yoshida, Jun Ichi ^b  

^a NAGOYA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Allylic alcohols and related systems; Chelation effects in Mizoroki Heck reaction; Chelation controlled Mizoroki Heck reactions; Directed Mizoroki Heck reaction of allylic amines; Multiple arylation; Other chelation controlled systems; Regioselective hydrogen elimination in allylic diol system; Vinyl ethers and controlling regioselectivity in Mizoroki Heck arylation; Vinyl silanes; Vinyl sulfoxides

Indexed keywords

EID: 84889455942     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470716076.ch7     Document Type: Chapter

References (60)

1. Hoveyda, A.H., Evans, D.A. and Fu, G.C. (1993) Substratedirectable chemical reactions. Chem. Rev., 93, 1307-70
2. Beak, P. and Meyers, A.I. (1986) Stereo-and regiocontrol by complex induced proximity effects: reactions of organolithium compounds. Acc. Chem. Res., 19, 356-63
3. Snieckus, V. (1990) Directed ortho metalation. Tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromatics. Chem. Rev., 90, 879-933
4. Beak, P., Basu, A., Gallagher, D.J. et al. (1996) Regioselective, diastereoselective, and enantioselective lithiation-substitution sequences: reaction pathways and synthetic applications. Acc. Chem. Res., 29, 552-60
5. Whisler, M.C., MacNeil, S., Snieckus, V. and Beak, P. (2004) Beyond thermodynamic acidity: a perspective on the complex-induced proximity effect (CIPE) in deprotonation reactions. Angew. Chem. Int. Ed., 43, 2206-25.
6. Oestreich, M. (2005) Neighbouring-group effects in Heck reactions. Eur. J. Org. Chem., 783-92
7. Oestreich,M. (2008) Directed Mizoroki-Heck reactions, in Topics in Organometallic Chemistry, Vol. 24 (ed. N. Chatani), Springer-Verlag, Heidelberg, pp. 169-92.
8. Andersson, C.-M., Larsson, J. and Hallberg, A. (1990) Chelation-controlled, palladium-catalyzed vinylic substitution reactions of vinyl ethers. 2-Arylethanal equivalents from aryl halides. J. Org. Chem., 55, 5757-61.
9. Breit, B. (2000) Controlling stereoselectivity with the aid of a reagent-directing group: hydroformylation, cuprate addition, and domino reaction sequences. Chem. Eur. J., 6, 1519-24
10. Jun, C.-H., Moon, C.W. and Lee, D.-Y. (2002) Chelation-assisted carbon-hydrogen and carbon-carbon bond activation by transition metal catalysts. Chem. Eur. J., 8, 2422-8
11. Itami, K., Mitsudo, K., Fujita, K. et al. (2004) Catalytic intermolecular Pauson-Khandtype reaction: strong directing effect of pyridylsilyl and pyrimidylsilyl groups and isolation of Ru complexes relevant to catalytic reaction. J. Am. Chem. Soc., 126, 11058-66
12. Adrio, J. and Carretero, J.C. (1999) The tert-butylsulfinyl group as a highly efficient chiral auxiliary in asymmetric Pauson-Khand reactions. J. Am. Chem. Soc., 121, 7411-2
13. Chatani, N., Tatamidani, H., Ie, Y. et al. (2001) The ruthenium-catalyzed reductive decarboxylation of ethers: catalytic reactions involving the cleavage of acyl-oxygen bonds of esters. J. Am. Chem. Soc., 123, 4849-50
14. Krauss, I.J., Wang, C.C.Y. and Leighton, J.L. (2001) Highly regioselective and diastereoselective directed hydroformylation of allylic ethers: a new approach to propionate aldol synthesis. J. Am. Chem. Soc., 123, 11514-5
15. Ko, S., Na, Y. and Chang, S. (2002) A novel chelation-assisted hydroesterification of alkenes via ruthenium catalysis. J. Am. Chem. Soc., 124, 750-1
16. Pastine, S.J., Gribkov, D.V. and Sames, D. (2006) sp3 C H bond arylation directed by amidine protecting group: α-arylation of pyrrolidines and piperidines. J. Am. Chem. Soc., 128, 14220-1.
17. Melpolder, J.B. and Heck, R.F. (1976) A palladium-catalyzed arylation of allylic alcohols with aryl halides. J. Org. Chem., 41, 265-72
18. Chalk, A.J. and Magennis, S.A. (1976) Palladium-catalyzed vinyl substitution reactions. I. A new synthesis of 2-and 3-phenyl substituted allylic alcohols, aldehydes, and ketones from allylic alcohols. J. Org. Chem., 41, 273-8.
19. Cacchi, S., Morera, E. and Ortar, G. (1984) Palladium-catalyzed vinylation of enol triflates. Tetrahedron Lett., 25, 2271-4
20. Bernocchi, E.,Cacchi, S.,Ciattini, P.G. et al. (1992) Palladiumcatalyzed vinylation of allylic alcohols with enol triflates. A convenient synthesis of conjugated dienols. Tetrahedron Lett., 33, 3073-6.
21. Jeffery, T. (1991) Palladium-catalyzed arylation of allylic alcohols: highly selective synthesis of β-aromatic carbonyl compounds or β-aromatic α,β-unsaturated alcohols. Tetrahedron Lett., 32, 2121-24
22. Jeffery, T. (1991) Palladium-catalyzed reaction of vinylic halides with allylic alcohols: a highly chemo-, regio-and stereo-controlled synthesis of conjugated dienols. J. Chem. Soc., Chem. Commun, 324-5
23. Jeffery, T. (1993) Palladium-catalyzed direct synthesis of optically active dienols. Tetrahedron Lett., 34, 1133-6.
24. Kang, S.-K., Lee, H.-W., Jang, S.-B. et al. (1996) Complete regioselection in palladium-catalyzed arylation and alkenylation of allylic alcohols with hypervalent iodonium salts. J. Org. Chem., 61, 2604-5.
25. Ono, K., Fugami, K., Tanaka, S. and Tamaru, Y. (1994) Palladium catalyzed arylation of N-alkyl O-allylic carbamates: synthesis of cinnamyl alcohols via Heck arylation. Tetrahedron Lett., 35, 4133-6.
26. Kang, S.-K., Jung, K.-Y., Park, C.-H. et al. (1995) Palladium-catalyzed arylation of allylic diols: highly selective synthesis of phenyl-substituted allylic diols. Tetrahedron Lett., 35, 6287-90.
27. Nilsson, K. and Hallberg, A. (1992) Synthesis of 1-propyl-3-(3-hydroxyphenyl)piperidine by regiocontrolled palladium-catalyzed arylation. J. Org. Chem., 57, 4015-7.
28. Olofsson, K., Larhed, M. and Hallberg, A. (2000) Highly regioselective palladium-catalyzed β-arylation of N,N-dialkylallylamines. J. Org. Chem., 65, 7235-9
29. Olofsson, K., Sahlin, H., Larhed, M. and Hallberg, A. (2001) Regioselective palladium-catalyzed synthesis of β-arylated primary allylamine equivalents by an efficient Pd N coordination. J. Org. Chem., 66, 544-9.
30. Larhed, M., Andersson, C.-M., and Hallberg, A. (1993) Chelation-controlled, palladiumcatalyzed arylation of vinyl ethers. Acta Chem. Scand., 47, 212-7
31. Larhed, M., Andersson, C.-M., and Hallberg, A. (1994) Chelation-controlled, palladium-catalyzed arylation of enol ethers with aryl triflates. Ligand control of selection for α-or β-arylation of [2-(dimethylamino)ethoxy]ethene. Tetrahedron, 50, 285-304
32. Stadler, A., von Schenck, H., Vallin, K.S.A. et al. (2004) Terminal Heck vinylations of chelating vinyl ethers. Adv. Synth. Catal., 346, 1773-81.
33. Badone, D. and Guzzi, U. (1993) Palladium-catalyzed β-arylation of modified vinyl ethers with aryl triflates. Tetrahedron Lett., 34, 3603-6.
34. Nilsson, P., Larhed, M. and Hallberg, A. (2001) Highly regioselective, sequential, and multiple palladium-catalyzed arylations of vinyl ethers carrying a coordinating auxiliary: an example of a Heck triarylation process. J. Am. Chem. Soc., 123, 8217-25.
35. Itami, K., Nokami, T., Ishimura, Y. et al. (2001) Diversity-oriented synthesis of multisubstituted olefins through the sequential integration of palladium-catalyzed cross-coupling reactions. 2-Pyridyldimethyl(vinyl)silane as a versatile platform for olefin synthesis. J. Am. Chem. Soc., 123, 11577-85.
36. Svennebring, A., Nilsson, P. and Larhed, M. (2004) Microwave-promoted and chelationcontrolled double arylations of terminal olefinic carbon of vinyl ethers. J. Org. Chem., 69, 3345-9.
37. Cabri, W. and Candiani, I. (1995) Recent developments and new perspectives in the Heck reaction. Acc. Chem. Res., 28, 2-7.
38. Nilsson, P., Larhed, M. and Hallberg, A. (2003) A new highly asymmetric chelation-controlled Heck arylation. J. Am. Chem. Soc., 125, 3430-1.
39. Itami, K., Mitsudo, K., Kamei, T. et al. (2000) Highly efficient carbopalladation across vinylsilane: dual role of the 2-PyMe2Si group as a directing group and as a phase tag. J. Am. Chem. Soc., 122, 12013-4.
40. Itami, K., Nokami, T. and Yoshida, J. (2001) Palladium-catalyzed cross-coupling reaction of alkenyldimethyl(2-pyridyl)silanes with organic halides: complete switch from the carbometalation pathway to the transmetalation pathway. J. Am. Chem. Soc., 123, 5600-1
41. Nokami, T., Itami, K. and Yoshida, J. (2004) Aqueous photo-dimerization using 2-pyridylsilyl group as a removable hydrophilic group. Chem. Lett., 33, 596-7
42. Itami, K., Ushiogi, Y., Nokami, T. et al. (2004) Stereoselective synthesis of multisubstituted butadienes through directed Mizoroki-Heck reaction and homocoupling reaction of vinyl(2-pyridyl)silane. Org. Lett., 6, 3695-8.
43. Itami, K., Kamei, T. and Yoshida, J. (2001) Unusually accelerated silylmethyl transfer from tin in Stille coupling: implication of coordination-driven transmetalation. J. Am. Chem. Soc., 123, 8773-9.
44. Itami, K., Ohashi, Y. and Yoshida, J. (2005) Triarylethene-based extended π-systems: programmable synthesis and photophysical properties. J. Org. Chem., 70, 2778-92.
45. Itami, K. and Yoshida, J. (2006) Multisubstituted olefins: platform synthesis and applications to materials science and pharmaceutical chemistry. Bull. Chem. Soc. Jpn., 79, 811-24
46. Itami, K. andYoshida, J. (2006) Platform synthesis: a useful strategy for rapid and systematic generation of molecular diversity. Chem. Eur. J., 12, 3966-74.
47. Itami, K., Mineno, M., Muraoka, N. and Yoshida, J. (2004) Sequential assembly strategy for tetrasubstituted olefin synthesis using vinyl 2-pyrimidyl sulfide as a platform. J. Am. Chem. Soc., 126, 11778-9.
48. Muraoka, N., Mineno, M., Itami, K. and Yoshida, J. (2005) Rapid synthesis of CDP840 with 2-pyrimidyl vinyl sulfide as a platform. J. Org. Chem., 70, 6933-6.
49. Buezo, N.D., Alonso, I. and Carretero, J.C. (1998) Sulfinyl group as a novel chiral auxiliary in asymmetric Heck reactions. J. Am. Chem. Soc., 120, 7129-30.
50. Alonso, I. and Carretero, J.C. (2001) Highly stereoselective synthesis of trisubstituted α,β-unsaturated sulfoxides by Heck reaction. J. Org. Chem., 66, 4453-6.
51. Buezo, N.D., de la Rosa, J.C., Priego, J. et al. (2001) Sulfoxides as stereochemical controllers in intermolecular Heck reactions. Chem. Eur. J., 7, 3890-900.
52. Buezo, N.D., Mancheño, O.G., and Carretero, J.C. (2000) The 2-(N,N-dimethylamino) phenylsulfinyl group as an efficient chiral auxiliary in intramolecular Heck reactions. Org. Lett., 2, 1451-4.
53. Mauleón, P., Núñez, A.A., Alonso, I. and Carretero, J.C. (2003) Palladium-catalyzed cascade reaction of α,β-unsaturated sulfones with aryl iodides. Chem. Eur. J., 9, 1511-20.
54. Llamas, T., Gómez Arrayás, R. and Carretero, J.C. (2004) Chelation-induced catalytic multiple arylation of allylic 2-pyridyl sulfones. Adv. Synth. Catal., 346, 1651-4.
55. Garg, N., Larhed, M. and Hallberg, A. (1998) Heck arylation of 1,2-cyclohexanedione and 2-ethoxy-2-cyclohexenone. J. Org. Chem., 63, 4158-62.
56. Jeong, S., Chen, X. and Harran, P.G. (1998) Macrocyclic triarylethylenes via Heck endocyclization: a system relevant to diazonamide synthesis. J. Org. Chem., 63, 8640-1.
57. Oestreich, M., Sempere-Culler, F. and Machotta, A.B. (2005) Catalytic desymmetrizing intramolecular Heck reaction: evidence for an unusual hydroxy-directed migratory insertion. Angew. Chem. Int. Ed., 44, 149-52.
58. Madin, A. and Overman, L.E. (1992) Controlling stereoselection in intramolecular Heck reactions by tailoring the palladium catalyst. Tetrahedron Lett., 33, 4859-62
59. Madin, A., O'Donnell, C.J., Oh, T. et al. (2005) Use of the intramolecular Heck reaction for forming congested quaternary carbon stereocenters. Stereocontrolled total synthesis of (±)-gelsemine. J. Am. Chem. Soc., 127, 18054-65.
60. Yoshida, J. and Itami, K. (2002) Tag strategy for separation and recovery. Chem. Rev., 102, 3693-716.