Copper-catalysed selective hydroamination reactions of alkynes

Nature Chemistry

Volumn 7, Issue 1, 2015, Pages 38-44

  Shi, Shi Liang ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AMINE; ATOMOXETINE; BENZHYDRYL DERIVATIVE; COPPER; CRESOL; DULOXETINE; FLUOXETINE; PHENYLPROPANOLAMINE; PROPYLAMINE; THIOPHENE DERIVATIVE; TOLTERODINE;

AMINATION; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKYNES; AMINATION; AMINES; ATOMOXETINE HYDROCHLORIDE; BENZHYDRYL COMPOUNDS; CATALYSIS; COPPER; CRESOLS; DULOXETINE HYDROCHLORIDE; FLUOXETINE; PHENYLPROPANOLAMINE; PROPYLAMINES; STEREOISOMERISM; THIOPHENES; TOLTERODINE TARTRATE;

EID: 84922780174     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.2131     Document Type: Article

References (48)

1. Trost, B. M. Selectivity: the key to synthetic efficiency. Science 219, 245-250 (1983).
2. Dewick, P. M. Medicinal Natural Products: A Biosynthetic Approach 3rd edn (Wiley, 2008).
3. Nugent, T. C. Chiral Amine Synthesis: Methods, Developments and Applications (Wiley, 2010).
4. Surry, D. S., Buchwald, S. L. Biaryl phosphane ligands in palladium-catalyzed amination. Angew. Chem. Int. Ed. 47, 6338-6361 (2008).
5. Surry, D. S., Buchwald, S. L. Dialkylbiaryl phosphines in Pd-catalyzed amination: a user's guide. Chem. Sci. 2, 27-50 (2011).
6. Robak, M. T., Herbage, M. A., Ellman, J. A. Synthesis and applications of tert-butanesulfinamide. Chem. Rev. 110, 3600-3740 (2010).
7. Roizen, J. L., Harvey, M. E., Du Bois, J. Metal-catalyzed nitrogen-atom transfer methods for the oxidation of aliphatic C-H bonds. Acc. Chem. Res. 45, 911-922 (2012).
8. Simon, R. C. et al. Regio-and stereoselective monoamination of diketones without protecting groups. Angew. Chem. Int. Ed. 51, 6713-6716 (2012).
9. Höhne, M., Kühl, S., Robins, K., Bornscheuer, U. T. Efficient asymmetric synthesis of chiral amines by combining transaminase and pyruvate decarboxylase. ChemBioChem 9, 363-365 (2008).
10. Hultzsch, K. C. Catalytic asymmetric hydroamination of non-activated olefins. Org. Biomol. Chem. 3, 1819-1824 (2005).
11. Hannedouche, J., Schulz, E. Asymmetric hydroamination: a survey of the most recent developments. Chem. Eur. J. 19, 4972-4985 (2013).
12. Müller, T. E., Hultzsch, K. C., Yus, M., Foubelo, F., Tada, M. Hydroamination: direct addition of amines to alkenes and alkynes. Chem. Rev. 108, 3795-3892 (2008).
13. Chinchilla, R., Nájera, C. Recent advances in Sonogashira reactions. Chem. Soc. Rev. 40, 5084-5121 (2011).
14. Trost, B. M., Weiss, A. H. The enantioselective addition of alkyne nucleophiles to carbonyl groups. Adv. Synth. Catal. 351, 963-983 (2009).
15. Habrant, D., Rauhala, V., Koskinen, A. M. P. Conversion of carbonyl compounds to alkynes: general overview and recent developments. Chem. Soc. Rev. 39, 2007-2017 (2010).
16. Severin, R., Doye, S. The catalytic hydroamination of alkynes. Chem. Soc. Rev. 36, 1407-1420 (2007).
17. Alonso, F., Beletskaya, I. P., Yus, M. Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes. Chem. Rev. 104, 3079-3160 (2004).
18. Zeng, X. Recent advances in catalytic sequential reactions involving hydroelement addition to carbon-carbon multiple bonds. Chem. Rev. 113, 6864-6900 (2013).
19. Li, L., Herzon, S. B. Regioselective reductive hydration of alkynes to form branched or linear alcohols. J. Am. Chem. Soc. 134, 17376-17379 (2012).
20. Li, L., Herzon, S. B. Temporal separation of catalytic activities allows anti-Markovnikov reductive functionalization of terminal alkynes. Nature Chem. 6, 22-27 (2014).
21. Zeng, M., Li, L., Herzon, S. B. A highly active and air-stable ruthenium complex for the ambient temperature anti-Markovnikov reductive hydration of terminal alkynes. J. Am. Chem. Soc. 136, 7058-7067 (2014).
22. Uehling, M. R., Rucker, R. P., Lalic, G. Catalytic anti-Markovnikov hydrobromination of alkynes. J. Am. Chem. Soc. 136, 8799-8803 (2014).
23. Zhu, S., Niljianskul, N., Buchwald, S. L. Enantio-and regioselective CuH-catalyzed hydroamination of alkenes. J. Am. Chem. Soc. 135, 15746?15749 (2013).
24. Miki, Y., Hirano, K., Satoh, T., Miura, M. Copper-catalyzed intermolecular regioselective hydroamination of styrenes with polymethylhydrosiloxane and hydroxylamines. Angew. Chem. Int. Ed. 52, 10830-10834 (2013).
25. Deutsch, C., Krause, N., Lipshutz, B. H. CuH-catalyzed reactions. Chem. Rev. 108, 2916-2927 (2008).
26. Mahoney, W. S., Stryker, J. M. Hydride-mediated homogeneous catalysis. Catalytic reduction of ?, ?-unsaturated ketones using [(Ph3P)CuH]6 and H2. J. Am. Chem. Soc. 111, 8818-8823 (1989).
27. Lipshutz, B. H., Keith, J., Papa, P., Vivian, R. A convenient, efficient method for conjugate reductions using catalytic quantities of Cu(I). Tetrahedron Lett. 39, 4627-4630 (1998).
28. Appella, D. H., Moritani, Y., Shintani, R., Ferreira, E. M., Buchwald, S. L. Asymmetric conjugate reduction of ?, ?-unsaturated esters using a chiral phosphine-copper catalyst. J. Am. Chem. Soc. 121, 9473-9474 (1999).
29. Moritani, Y., Appella, D. H., Jurkauskas, V., Buchwald, S. L. Synthesis of ?-alkyl cyclopentanones in high enantiomeric excess via copper-catalyzed asymmetric conjugate reduction. J. Am. Chem. Soc. 122, 6797-6798 (2000).
30. Yun, J., Buchwald, S. L. One-pot synthesis of enantiomerically enriched 2, 3-disubstituted cyclopentanones via copper-catalyzed 1, 4-reduction and alkylation. Org. Lett. 3, 1129-1131 (2001).
31. Jurkauskas, V., Buchwald, S. L. Dynamic kinetic resolution via asymmetric conjugate reduction: enantio-and diastereoselective synthesis of 2, 4-dialkyl cyclopentanones. J. Am. Chem. Soc. 124, 2892-2893 (2002).
32. Rainka, M. P., Aye, Y., Buchwald, S. L. Copper-catalyzed asymmetric conjugate reduction as a route to novel ?-azaheterocyclic acid derivatives. Proc. Natl Acad. Sci. USA 101, 5821-5823 (2004).
33. Erdik, E., Ay, M. Electrophilic amination of carbanions. Chem. Rev. 89, 1947-1980 (1989).
34. Barker, T. J., Jarvo, E. R. Developments in transition-metal-catalyzed reactions using electrophilic nitrogen sources. Synthesis 24, 3954-3964 (2011).
35. Berman, A. M., Johnson, J. S. Copper-catalyzed electrophilic amination of diorganozinc reagents. J. Am. Chem. Soc. 126, 5680-5681 (2004).
36. Campbell, M. J., Johnson, J. S. Mechanistic studies of the copper-catalyzed electrophilic amination of diorganozinc reagents and development of a zinc-free protocol. Org. Lett. 9, 1521-1524 (2007).
37. Xu, P-F., Wang, W. Catalytic Cascade Reactions (Wiley, 2014).
38. Daeuble, J. F., McGettigan, C., Stryker, J. M. Selective reduction of alkynes to cis-alkenes by hydrometallation using [(Ph3P)CuH]6. Tetrahedron Lett. 31, 2397-2400 (1990).
39. Semba, K., Fujihara, T., Xu, T., Terao, J., Tsuji, Y. Copper-catalyzed highly selective semihydrogenation of non-polar carbon-carbon multiple bonds using a silane and an alcohol. Adv. Synth. Catal. 354, 1542-1550 (2012).
40. Whittaker, A. M., Lalic, G. Monophasic catalytic system for the selective semireduction of alkynes. Org. Lett. 15, 1112-1115 (2013).
41. Field, L. D., Messerle, B. A., Wren, S. L. One-pot tandem hydroamination/hydrosilation catalyzed by cationic iridium(I) complexes. Organometallics 22, 4393-4395 (2003).
42. Heutling, A., Pohlki, F., Bytschkov, I., Doye, S. Hydroamination/hydrosilylation sequence catalyzed by titanium complexes. Angew. Chem. Int. Ed. 44, 2951-2954 (2005).
43. Hesp, K. D., Stradiotto, M. Stereo-and regioselective gold-catalyzed hydroamination of internal alkynes with dialkylamines. J. Am. Chem. Soc. 132, 18026-18029 (2010).
44. Jozsef, B. et al. Process for preparation of duloxetine and intermediates. International patent WO 2008078124 (2008).
45. Wu, F., Chen, G., Yang, X. Process for preparation of propylamine derivatives and application in manufacturing tomoxetine. Chinese patent CN1948277 (2007).
46. Bhandari, K., Srivastava, S., Shanker, G., Nath, C. Substituted propanolamines and alkylamines derived from fluoxetine as potent appetite suppressants. Bioorg. Med. Chem. 13, 1739-1747 (2005).
47. Paras, N. A., Simmons, B., MacMillan, D. W. C. A process for the rapid removal of dialkylamino-substituents from aromatic rings. Application to the expedient synthesis of (R)-tolterodine. Tetrahedron 65, 323-238 (2009).
48. Rupnicki, L., Saxena, A., Lam, H. W. Aromatic heterocycles as activating groups for asymmetric conjugate addition reactions: enantioselective coppercatalyzed reduction of 2-alkenylheteroarenes. J. Am. Chem. Soc. 131, 10386-10387 (2009).