Design and implementation of new, silicon-based, cross-coupling reactions: Importance of silicon-oxygen bonds

Accounts of Chemical Research

Volumn 35, Issue 10, 2002, Pages 835-846

  Denmark, Scott E ^a   Sweis, Ramzi F ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL GROUP; ETHER DERIVATIVE; FLUORIDE; ORGANIC COMPOUND; ORGANOSILICON DERIVATIVE; OXYGEN; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SILANE DERIVATIVE; SILETANE DERIVATIVE; SILICON; SILICON DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; MOLECULAR DYNAMICS; REACTION ANALYSIS; STEREOSPECIFICITY; SYNTHESIS;

CATALYSIS; ETHERS; MOLECULAR STRUCTURE; ORGANOSILICON COMPOUNDS; OXYGEN; PALLADIUM; SILICON;

EID: 0036798587     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar020001r     Document Type: Article

References (54)

1. Two Organic Chemists Share Nobel Prize. Chem. Eng. News 1979, 57 (43), 6-7.
2. (a) Stille, J. K. The Palladium-Catalyzed Cross-Coupling Reactions of Organotin Reagents with Organic Electrophiles. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
3. (b) Mitchell, T. N. Organotin Reagents in Cross-Coupling, In Metal Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinhein, Germany, 1998; Chapter 4.
4. (c) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction. Org. React. 1998, 50, 1-657.
5. (a) Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457-2483.
6. (b) Suzuki, A. Recent Advances in the Cross-Coupling Reactions of Organoboron Derivatives with Organic Electrophiles, 1995-1998. J. Organomet. Chem. 1999, 576, 147-168.
7. Hatanaka, Y.; Hiyama, T. Cross-Coupling of Organosilanes with Organic Halides Mediated by Palladium Catalyst and Tris(diethylamino)sulfonium Difluorotrimethylsilicate. J. Org. Chem. 1988, 53, 918-920.
8. Hiyama, T. Organosilicon Compounds in Cross-Coupling Reactions. In Metal Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinhein, Germany, 1998; Chapter 10.
9. (a) Tamao, K.; Kobayashi, K.; Ito, Y. Palladium-Catalyzed Cross-Coupling Reaction of Alkenylalkoxysilanes with Aryl and Alkenyl Halides in the Presence of a Fluoride Ion. Tetrahedron Lett. 1989, 30, 6051-6054.
10. (b) Mowery, M. E.; DeShong, P. Cross-Coupling Reactions of Hypervalent Siloxane Derivatives: An Alternative to Stille and Suzuki Couplings. J. Org. Chem. 1999, 64, 1684-1688.
11. (c) Mowery, M. E.; DeShong, P. Synthesis of Unsymmetrical Biaryls by Palladium-Catalyzed Cross-Coupling Reactions of Arenes with Tetrabutylammonium Triphenyldifluorosilicate, a Hypervalent Silicon Reagent. J. Org. Chem. 1999, 64, 3266-3270.
12. (d) Mowery, M. E.; DeShong, P. Improvements in Cross Coupling Reactions of Hypervalent Siloxane Derivatives. Org. Lett. 1999, 1, 2137-2140.
13. (e) Lee, H. M.; Nolan, S. P. Efficient Cross-Coupling Reactions of Aryl Chlorides and Bromides with Phenyl- or Vinyltrimethoxysilane Mediated by a Palladium/Imidazolium Chloride System. Org. Lett. 2000, 2, 2053-2055.
14. (a) Denmark, S. E.; Griedel, B. D.; Coe, D. M.; Schnute, M. E. Chemistry of Enoxysilacyclobutanes: Highly Selective Uncatalyzed Aldol Additions. J. Am. Chem. Soc. 1994, 116, 7026-7043.
15. (b) Denmark, S. E.; Griedel, B. D. Chemistry of Enoxysilacyclobutanes. 3. Uncatalyzed, Syn-Selective, Asymmetric Aldol Additions. J. Org. Chem. 1994, 59, 5136-5138.
16. Denmark, S. E.; Jacobs, R. T.; Dai-Ho, G.; Wilson, S. Synthesis, Structure, and Reactivity of an Organogermanium Lewis Acid. Organometallics 1990, 9, 3015-3019.
17. Denmark, S. E.; Choi, J. Y. Highly Stereospecific, Cross-Coupling Reactions of Alkenylsilacyclobutanes. J. Am. Chem. Soc. 1999, 121, 5821-5822.
18. Denmark, S. E.; Wang, Z. 1-Methyl-1-vinyl- and 1-Methyl-1-(prop-2-enyl)silacyclobutane: Reagents for Palladium-Catalyzed CrossCoupling Reactions of Aryl Halides. Synthesis 2000, 999-1003.
19. (a) Torsell, K. G. B. Natural Product Chemistry; Wiley: Chichester, U.K., 1983.
20. (b) Thompson, R. H. The Chemistry of Natural Products; Blackie and Son: Glaskow, U.K., 1985.
21. (c) Roncali, J. Conjugated Poly(thiophenes): Synthesis, Functionalization, and Applications. Chem. Rev. 1992, 92, 711-738.
22. (a) Stanforth, S. P. Catalytic Cross-Coupling Reactions in Biaryl Synthesis. Tetrahedron 1998, 54, 263-303.
23. (b) Bringmann, G.; Walter, R.; Weirich, R. The Directed Synthesis of Biaryl Compounds-Modern Concepts and Strategies. Angew. Chem., Int. Ed. Engl. 1990, 29, 977-991.
24. (c) Sainsbury, M. Modern Methods of ArylAryl Bond Formation. Tetrahedron 1980, 36, 3327-3359.
25. Denmark, S. E.; Wehrli, D.; Choi, J. Y. Convergence of Mechanistic Pathways in the Palladium(0)-Catalyzed Cross-Coupling of Alkenylsilacyclobutanes and Alkenylsilanols. Org. Lett. 2000, 2, 2491-2494.
26. Martin, J. S.; Fujiwara, F. Y. High-Resolution NMR Spectra of Bifluoride Ion and its Homolog. Can. J. Chem. 1971, 49, 3071-3073.
27. Wehrli, D.; Sweis, R. F. Unpublished results from these laboratories.
28. Yoshida has recently described that the use of 2-pyridyldimethylalkenylsilanes in fluoride-promoted cross-coupling actually involves intermediates akin to those described herein: Itami, K.; Nokami, T.; Ishimura, Y.; Mitsudo, K.; Kamel, T.; Yoshida, J. Diversity-Oriented Synthesis of Multisubstituted Olefins through the Sequential Integration of Palladium-Catalyzed Cross Coupling Reactions. Pyridyldimethyl(vinyl)silane as a Versatile Platform for Olefin Synthesis. J. Am. Chem. Soc. 2001, 123, 11577-11585.
29. Chang has recently reported a palladium-catalyzed coupling of alkynyl silanols in the presence of TBAF: Chang, S.; Yang, S. H.; Lee, P. H. Pd-Catalyzed Cross-Coupling of Alkynylsilanols with lodobenzenes. Tetrahedron Lett. 2001, 42, 4833-4835.
30. (E)-25 and (Z)-25 were easily synthesized in one step from the corresponding alkenyl halides via lithiation and trapping with hexamethylcyclotrisiloxane.
31. (a) Hirabayashi, K.; Takahisa, E.; Nishihara, Y.; Mori, A.; Hiyama, T. A Facile Preparation and Cyclopropanation of 1-Alkenylsilanols. Bull. Chem. Soc. Jpn. 1998, 71, 2409-2417.
32. (b) Sieburth, S. McN.; Fensterbank, L. Silanol Reactivity: Evaluation of Silanolate as a Metalation-Directing Group. J. Org. Chem. 1993, 58, 6314-6318.
33. (c) Sieburth, S. McN.; Mu, W. Silanol Synthesis: Reaction of Hexaphenylcyclotrisiloxane with Organometallic Reagents. J. Org. Chem. 1993, 58, 7584-7586.
34. Denmark, S. E.; Wehrli, D. Highly Stereospecific, Palladium-Catalyzed Cross-Coupling of Alkenylsilanols. Org. Lett. 2000, 2, 565-568.
35. Although the yields from 25 are reported to be lower than those from 18, this fact is an artifact of purification to analytical standards; the assayed yield is the same.
36. Cine refers to the product arising from coupling at the β-position to silicon.
37. Denmark, S. E.; Pan, W. Efficient and Stereoselective Prenylation by Cross-Coupling with Highly Substituted Alkenylsilanols. J. Organomet. Chem. 2002, in press.
38. Denmark, S. E.; Neuville, L. Mild and General Cross-Coupling of (α-Alkoxyvinyl)silanols and -silyl Hydrides. Org. Lett. 2000, 2, 3221-3224.
39. Macleod, D.; Moorcroft, D.; Quayle, P.; Dorrity, M. R. J.; Malone, J. F.; Davies, G. M. The Pd(0)-Catalysed Coupling Reactions of 2-(Tri-n-butylstannyl)-3,4-dihydofuran and -5,6-dihydropyran. Tetrahedron Lett. 1990, 31, 6077-6080.
40. Deneux, M.; Akhrem, I. C.; Avetissian, D. V.; Myssoff, E. I.; Vol'pin, M. E. Reactions des Trialkylsilanes Catalysees par L'ion Fluorure. Bull. Soc. Chim. Fr. 1973, 2638-2642.
41. Denmark, S. E.; Wang, Z. Cross-Coupling of Vinylpolysiloxanes with Aryl Iodides. J. Organomet. Chem. 2001, 624, 372-375.
42. Denmark, S. E.; Wang, Z. Highly Selective Hydrocarbation of Terminal Alkynes via Pt-Catalyzed Hydrosilylation/Pd-Catalyzed Cross-Coupling Reactions. Org. Lett. 2001, 3, 1073-1076.
43. DVDS: 1,3-divinyl-1,1,3,3-tetramethyldisiloxane.
44. Using other silanes and platinum sources that gave 100% conversion to the coupling product, 12-16% of the α-regioisomer was observed from the hydrosilylation step.
45. Denmark, S. E.; Pan, W. Intramolecular Hydrosilylation and Silicon-Assisted Cross-Coupling: An Efficient Route to Trisubstituted Homoallylic Alcohols. Org. Lett. 2001, 3, 61-64.
46. A complementary anti hydrosilylation/cross-coupling process that uses a ruthenium-based catalyst has recently been developed. Denmark, S. E.; Pan, W. Manuscript submitted for publication.
47. Extension of this approach to the synthesis of allylic alcohols has also been achieved using a novel class of unsymmetrical disiloxanes. Denmark, S. E.; Pan, W. Manuscript in preparation.
48. For a recent review on RCM, see the following: Furstner, A. Olefin Metathesis and Beyond. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
49. (a) Denmark, S. E.; Yang, S.-M. Sequential Ring-Closing Metathesis and Silicon-Assisted Cross-Coupling Reactions: Stereo-controlled Synthesis of Highly Substituted Unsaturated Alcohols. Org. Lett. 2001, 3, 1749-1752.
50. (b) Denmark, S. E.; Yang, S.-M. Intramolecular Silicon-Assisted Cross Coupling Reactions: General Synthesis of Medium-Sized Rings Containing a 1,3-cis-cis Diene Unit. J. Am. Chem. Soc. 2002, 124, 2102-2103.
51. Denmark, S. E.; Sweis, R. F. Fluoride-Free Cross-Coupling of Organosilanols. J. Am. Chem. Soc. 2001, 123, 6439-6440.
52. 2O as a coupling activator, though at elevated temperatures: (a) Hirabayashi, L.; Kawashima, J.; Nishihara, Y.; Mori, A.; Hiyama, T. A New Transformation of Silanols. Palladium-Catalyzed Cross-Coupling with Organic Halides in the Presence of Silver(I) Oxide. Org. Lett. 1999, 1, 299-301. (b) Hirabayashi, K. Mori, A.; Kawashima, J.; Suguro, M.; Nishihara, Y.; Hiyama, T. Palladium-Catalyzed Cross-Coupling of Silanols, Silanediols, and Silanetriols Promoted by Silver(I) Oxide. J. Org. Chem. 2000, 65, 5342-5349.
53. 2O as a coupling activator, though at elevated temperatures: (a) Hirabayashi, L.; Kawashima, J.; Nishihara, Y.; Mori, A.; Hiyama, T. A New Transformation of Silanols. Palladium-Catalyzed Cross-Coupling with Organic Halides in the Presence of Silver(I) Oxide. Org. Lett. 1999, 1, 299-301. (b) Hirabayashi, K. Mori, A.; Kawashima, J.; Suguro, M.; Nishihara, Y.; Hiyama, T. Palladium-Catalyzed Cross-Coupling of Silanols, Silanediols, and Silanetriols Promoted by Silver(I) Oxide. J. Org. Chem. 2000, 65, 5342-5349.
54. Potassium trimethylsilanolate (Aldrich), $63/mol. Tetrabutylammonium fluoride trihydrate (Fluka), $624/mol.