Stille cross-couplings of unactivated secondary alkyl halides using monoorganotin reagents

Journal of the American Chemical Society

Volumn 127, Issue 2, 2005, Pages 510-511

  Powell, David A ^a   Maki, Toshihide ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,2' BIPYRIDINE; BROMINE DERIVATIVE; HALIDE; IODINE DERIVATIVE; ISOBUTANOL; NICKEL; NICKEL CHLORIDE; ORGANOTIN COMPOUND; PALLADIUM; REAGENT; TRICHLOROTIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CYCLIZATION; GAS CHROMATOGRAPHY; STILLE REACTION; STOICHIOMETRY; SYNTHESIS;

CATALYSIS; HYDROCARBONS; HYDROCARBONS, HALOGENATED; ORGANOMETALLIC COMPOUNDS; TIN;

EID: 12944309312     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0436300     Document Type: Article

References (40)

1. For reviews, see: (a) Kosugi, M.; Fugami, K. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; Wiley-Interscience: New York, 2002; pp 263-283. (b) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998; Chapter 4. (c) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (d) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704-4734.
2. For reviews, see: (a) Kosugi, M.; Fugami, K. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; Wiley-Interscience: New York, 2002; pp 263-283. (b) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998; Chapter 4. (c) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (d) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704-4734.
3. For reviews, see: (a) Kosugi, M.; Fugami, K. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; Wiley-Interscience: New York, 2002; pp 263-283. (b) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998; Chapter 4. (c) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (d) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704-4734.
4. For reviews, see: (a) Kosugi, M.; Fugami, K. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; Wiley-Interscience: New York, 2002; pp 263-283. (b) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998; Chapter 4. (c) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (d) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704-4734.
5. Deng, H.; Jung, J.-K.; Liu, T.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 9032-9034.
6. Nicolaou, K. C.; Li, Y.; Sugita, K.; Monenschein, H.; Guntupalli, P.; Mitchell, H. J.; Fylaktakidou, K. C.; Vourloumis, D.; Giannakakou, P.; O'Brate, A. J. Am. Chem. Soc. 2003, 125, 15443-15454.
7. Yu, H.-h.; Xu, B.; Swager, T. M. J. Am. Chem. Soc. 2003, 125, 1142-1143.
8. "The most toxic organotin chemicals belong to the class of the triorganotin compounds": Bulten, E. J.; Meinema, H. A. In Metals and Their Compounds in the Environment; Merian, E., Ed.; VCH: New York, 1991; Chapter II.30, p 1243.
9. For examples and leading references, see: (a) (Polymer-supported tin reagents) Kuhn, H.; Neumann, W. P. Synlett 1994, 123-124. Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2534-2537. (b) (Fluorous tin reagents) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341-8349. (c) (Catalytic hydrostannation/Stille reaction) Gallagher, W. P.; Terstiege, I.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 2001, 123, 3194-3204.
10. For examples and leading references, see: (a) (Polymer-supported tin reagents) Kuhn, H.; Neumann, W. P. Synlett 1994, 123-124. Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2534-2537. (b) (Fluorous tin reagents) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341-8349. (c) (Catalytic hydrostannation/Stille reaction) Gallagher, W. P.; Terstiege, I.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 2001, 123, 3194-3204.
11. For examples and leading references, see: (a) (Polymer-supported tin reagents) Kuhn, H.; Neumann, W. P. Synlett 1994, 123-124. Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2534-2537. (b) (Fluorous tin reagents) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341-8349. (c) (Catalytic hydrostannation/Stille reaction) Gallagher, W. P.; Terstiege, I.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 2001, 123, 3194-3204.
12. For examples and leading references, see: (a) (Polymer-supported tin reagents) Kuhn, H.; Neumann, W. P. Synlett 1994, 123-124. Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Murphy, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2534-2537. (b) (Fluorous tin reagents) Hoshino, M.; Degenkolb, P.; Curran, D. P. J. Org. Chem. 1997, 62, 8341-8349. (c) (Catalytic hydrostannation/Stille reaction) Gallagher, W. P.; Terstiege, I.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 2001, 123, 3194-3204.
13. (a) For Stille couplings that employ trichloroorganotin reagents, see: Roshchin, A. I.; Bumagin, N. A.; Beletskaya, I. P. Tetrahedron Lett. 1995, 36, 125-128. Rai, R.; Aubrecht, K. B.; Collum, D. B. Tetrahedron Lett. 1995, 36, 3111-3114.
14. (a) For Stille couplings that employ trichloroorganotin reagents, see: Roshchin, A. I.; Bumagin, N. A.; Beletskaya, I. P. Tetrahedron Lett. 1995, 36, 125-128. Rai, R.; Aubrecht, K. B.; Collum, D. B. Tetrahedron Lett. 1995, 36, 3111-3114.
15. (b) For Stille couplings that employ other monoorganotin reagents, see: Fouquet, E.; Pereyre, M.; Rodriguez, A. L. J. Org. Chem. 1997, 62, 5242-5243.
16. "Inorganic tin salts are generally acknowledged to be of a low order of toxicity": see ref 5.
17. For leading references, see: (a) Cárdenas, D. J. Angew. Chem., Int. Ed. 2003, 42, 384-387. (b) Netherton, M. R.; Fu, G. C. Adv. Synth. Catal. In press (nickel-catalyzed processes). (c) Powell, D. A.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 7788-7789.
18. For leading references, see: (a) Cárdenas, D. J. Angew. Chem., Int. Ed. 2003, 42, 384-387. (b) Netherton, M. R.; Fu, G. C. Adv. Synth. Catal. In press (nickel-catalyzed processes). (c) Powell, D. A.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 7788-7789.
19. For leading references, see: (a) Cárdenas, D. J. Angew. Chem., Int. Ed. 2003, 42, 384-387. (b) Netherton, M. R.; Fu, G. C. Adv. Synth. Catal. In press (nickel-catalyzed processes). (c) Powell, D. A.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 7788-7789.
20. Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 14726-14727.
21. Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 1340-1341.
22. Copper-, cobalt-, and iron-based methods have been developed for couplings of more reactive Grignard reagents: (a) Donkervoort, J. G.; Vicario, J. L.; Jastrzebski, J. T. B. H.; Gossage, R. A.; Cahiez, G.; van Koten, G. J. Organomet. Chem. 1998, 558, 61-69 (copper). (b) Tsuji, T.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2002, 41, 4137-4139 (cobalt). (c) Brinker, U. H.; König, L. Chem. Ber. 1983, 116, 882-893 (iron). (d) Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 3686-3687 (iron). (e) Nagano, T.; Hayashi, T. Org. Lett. 2004, 6, 1297-1299 (iron). (f) Martin, R.; Fürstner, A. Angew. Chem., Int. Ed. 2004, 43, 3955-3957 (iron).
23. Copper-, cobalt-, and iron-based methods have been developed for couplings of more reactive Grignard reagents: (a) Donkervoort, J. G.; Vicario, J. L.; Jastrzebski, J. T. B. H.; Gossage, R. A.; Cahiez, G.; van Koten, G. J. Organomet. Chem. 1998, 558, 61-69 (copper). (b) Tsuji, T.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2002, 41, 4137-4139 (cobalt). (c) Brinker, U. H.; König, L. Chem. Ber. 1983, 116, 882-893 (iron). (d) Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 3686-3687 (iron). (e) Nagano, T.; Hayashi, T. Org. Lett. 2004, 6, 1297-1299 (iron). (f) Martin, R.; Fürstner, A. Angew. Chem., Int. Ed. 2004, 43, 3955-3957 (iron).
24. Copper-, cobalt-, and iron-based methods have been developed for couplings of more reactive Grignard reagents: (a) Donkervoort, J. G.; Vicario, J. L.; Jastrzebski, J. T. B. H.; Gossage, R. A.; Cahiez, G.; van Koten, G. J. Organomet. Chem. 1998, 558, 61-69 (copper). (b) Tsuji, T.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2002, 41, 4137-4139 (cobalt). (c) Brinker, U. H.; König, L. Chem. Ber. 1983, 116, 882-893 (iron). (d) Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 3686-3687 (iron). (e) Nagano, T.; Hayashi, T. Org. Lett. 2004, 6, 1297-1299 (iron). (f) Martin, R.; Fürstner, A. Angew. Chem., Int. Ed. 2004, 43, 3955-3957 (iron).
25. Copper-, cobalt-, and iron-based methods have been developed for couplings of more reactive Grignard reagents: (a) Donkervoort, J. G.; Vicario, J. L.; Jastrzebski, J. T. B. H.; Gossage, R. A.; Cahiez, G.; van Koten, G. J. Organomet. Chem. 1998, 558, 61-69 (copper). (b) Tsuji, T.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2002, 41, 4137-4139 (cobalt). (c) Brinker, U. H.; König, L. Chem. Ber. 1983, 116, 882-893 (iron). (d) Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 3686-3687 (iron). (e) Nagano, T.; Hayashi, T. Org. Lett. 2004, 6, 1297-1299 (iron). (f) Martin, R.; Fürstner, A. Angew. Chem., Int. Ed. 2004, 43, 3955-3957 (iron).
26. Copper-, cobalt-, and iron-based methods have been developed for couplings of more reactive Grignard reagents: (a) Donkervoort, J. G.; Vicario, J. L.; Jastrzebski, J. T. B. H.; Gossage, R. A.; Cahiez, G.; van Koten, G. J. Organomet. Chem. 1998, 558, 61-69 (copper). (b) Tsuji, T.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2002, 41, 4137-4139 (cobalt). (c) Brinker, U. H.; König, L. Chem. Ber. 1983, 116, 882-893 (iron). (d) Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 3686-3687 (iron). (e) Nagano, T.; Hayashi, T. Org. Lett. 2004, 6, 1297-1299 (iron). (f) Martin, R.; Fürstner, A. Angew. Chem., Int. Ed. 2004, 43, 3955-3957 (iron).
27. Copper-, cobalt-, and iron-based methods have been developed for couplings of more reactive Grignard reagents: (a) Donkervoort, J. G.; Vicario, J. L.; Jastrzebski, J. T. B. H.; Gossage, R. A.; Cahiez, G.; van Koten, G. J. Organomet. Chem. 1998, 558, 61-69 (copper). (b) Tsuji, T.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2002, 41, 4137-4139 (cobalt). (c) Brinker, U. H.; König, L. Chem. Ber. 1983, 116, 882-893 (iron). (d) Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 3686-3687 (iron). (e) Nagano, T.; Hayashi, T. Org. Lett. 2004, 6, 1297-1299 (iron). (f) Martin, R.; Fürstner, A. Angew. Chem., Int. Ed. 2004, 43, 3955-3957 (iron).
28. For related three-component couplings of secondary alkyl halides with olefins and Grignard reagents, see: (a) Mizutani, K.; Shinokubo, H.; Oshima, K. Org. Lett. 2003, 5, 3959-3961. (b) Terao, J.; Nu, S.; Chowdhury, F. A.; Nakamura, A.; Kambe, N. Adv. Synth. Catal. 2004, 346, 905-908.
29. For related three-component couplings of secondary alkyl halides with olefins and Grignard reagents, see: (a) Mizutani, K.; Shinokubo, H.; Oshima, K. Org. Lett. 2003, 5, 3959-3961. (b) Terao, J.; Nu, S.; Chowdhury, F. A.; Nakamura, A.; Kambe, N. Adv. Synth. Catal. 2004, 346, 905-908.
30. 2, $5900/mol.
31. The role of KOt-Bu may be to generate a hypervalent tin species that undergoes efficient transmetalation. For early studies of the use of hypervalent tin compounds in Stille reactions, see: (a) Vedejs, E.; Haight, A. R.; Moss, W. O. J. Am. Chem. Soc. 1992, 114, 6556-6558. (b) Brown, J. M.; Pearson, M.; Jastrzebski, J. T. B. H.; van Koten, G. J. Chem. Soc., Chem. Commun. 1992, 1440-1441. (c) Martinez, A. G.; Barcina, J. O.; Cerezo, A. de F.; Subramanian, L. R. Synlett 1994, 1047-1048.
32. The role of KOt-Bu may be to generate a hypervalent tin species that undergoes efficient transmetalation. For early studies of the use of hypervalent tin compounds in Stille reactions, see: (a) Vedejs, E.; Haight, A. R.; Moss, W. O. J. Am. Chem. Soc. 1992, 114, 6556-6558. (b) Brown, J. M.; Pearson, M.; Jastrzebski, J. T. B. H.; van Koten, G. J. Chem. Soc., Chem. Commun. 1992, 1440-1441. (c) Martinez, A. G.; Barcina, J. O.; Cerezo, A. de F.; Subramanian, L. R. Synlett 1994, 1047-1048.
33. The role of KOt-Bu may be to generate a hypervalent tin species that undergoes efficient transmetalation. For early studies of the use of hypervalent tin compounds in Stille reactions, see: (a) Vedejs, E.; Haight, A. R.; Moss, W. O. J. Am. Chem. Soc. 1992, 114, 6556-6558. (b) Brown, J. M.; Pearson, M.; Jastrzebski, J. T. B. H.; van Koten, G. J. Chem. Soc., Chem. Commun. 1992, 1440-1441. (c) Martinez, A. G.; Barcina, J. O.; Cerezo, A. de F.; Subramanian, L. R. Synlett 1994, 1047-1048.
34. 3Sn-Bu, secondary alkyl tosylates, and secondary alkyl chlorides are not suitable cross-coupling partners. (c) The presence of functional groups on the alkyl halide can lead to significantly diminished reaction efficiency. For example, certain substrates that contain ketones, secondary amines, imides, and nitrites cross-couple in <20% yield. (d) The reaction is moisture-sensitive. (e) According to ICP-MS analysis, the tin contamination in the product (after chromatography) is less than 5 ppm.
35. Wood, M. E. In Science of Synthesis; Moloney, M. G., Ed.; Georg Thieme Verlag: Stuttgart, 2003; Vol. 5, Section 5.2.8.5.2.
36. For an interesting recent mechanistic study, see: Anderson, T. J.; Jones, G. D.; Vicic, D. A. J. Am. Chem. Soc. 2004, 126, 8100-8101.
37. (a) Pandey, G.; Rao, K. S. S. P.; Palit, D. K.; Mittal, J. P. J. Org. Chem. 1998, 63, 3968-3978.
38. (b) Hackmann, C.; Schäfer, H. J. Tetrahedron 1993, 49, 4559-4574.
39. (c) Mayer, S.; Prandi, J.; Bamhaoud, T.; Bakkas, S.; Guillou, O. Tetrahedron 1998, 54, 8753-8770.
40. For a similar Co-catalyzed reaction of Grignard reagents, see: Wakabayashi, K.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 5374-5375.