Alkynes as allylmetal equivalents in redox-triggered C-C couplings to primary alcohols: (Z)-homoallylic alcohols via ruthenium-catalyzed propargyl C-H oxidative addition

Journal of the American Chemical Society

Volumn 136, Issue 34, 2014, Pages 11902-11905

  Park, Boyoung Y ^a   Nguyen, Khoa D ^a   Chaulagain, Mani Raj ^a   Komanduri, Venukrishnan ^a   Krische, Michael J ^a  

^a University of Texas at Austin   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; OLEFINS; RUTHENIUM;

ACID-BASE REACTIONS; CATALYTIC MECHANISMS; DEUTERIUM LABELING; HOMOALLYLIC ALCOHOL; ISOTOPIC COMPOSITION; OXIDATIVE COUPLINGS; PRIMARY ALCOHOLS; RUTHENIUM CATALYSTS; ALLYLMETALS; C-C COUPLING; C-H OXIDATIVE; PROPARGYL;

PRASEODYMIUM COMPOUNDS;

ALCOHOL DERIVATIVE; ALKYNE DERIVATIVE; DEUTERIUM; HOMOALLYLIC ALCOHOL; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG; ALKYNE; ALLYL COMPOUND; ORGANOMETALLIC COMPOUND; PROPANOL; PROPARGYL ALCOHOL; RUTHENIUM; ACID; ALKENE; ALLYLMETAL; BASE; CARBON; HYDROGEN; METAL DERIVATIVE;

ACID BASE BALANCE; ALLYLATION; ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; GEOMETRY; OXIDATIVE COUPLING; STEREOCHEMISTRY; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; CHEMICAL COMPOSITION; COMPLEX FORMATION; COVALENT BOND; ISOTOPE LABELING; OXIDATION REDUCTION POTENTIAL;

ALCOHOLS; ALKYNES; ALLYL COMPOUNDS; CATALYSIS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PROPANOLS; RUTHENIUM; STEREOISOMERISM;

EID: 84906760391     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja505962w     Document Type: Article

References (58)

1. Ramachandran, P. V. Aldrichimica Acta 2002, 35, 23
2. Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763
3. Yu, C.-M.; Youn, J.; Jung, H.-K. Bull. Korean Chem. Soc. 2006, 27, 463
4. Marek, I.; Sklute, G. Chem. Commun. 2007, 1683
5. Hall, D. G. Synlett 2007, 1644
6. Lachance, H.; Hall, D. G. Org. React. 2008, 73, 1
7. Yus, M.; González-Gómez, J. C.; Foubelo, F. Chem. Rev. 2011, 111, 7774
8. Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C. Chem. Soc. Rev. 1999, 28, 169
9. Bandini, M.; Cozzi, P. G.; Umani-Ronchi, A. Chem. Commun. 2002, 919
10. Hargaden, G. C.; Guiry, P. J. Adv. Synth. Catal. 2007, 349, 2407
11. Bower, J. F.; Krische, M. J. Top. Organomet. Chem. 2011, 34, 107
12. Hassan, A.; Krische, M. J. Org. Process Res. Dev. 2011, 15, 1236
13. Moran, J.; Krische, M. J. Pure Appl. Chem. 2012, 84, 1729
14. Dechert-Schmitt, A.-M. R.; Schmitt, D. C.; Gao, X.; Itoh, T.; Krische, M. J. Nat. Prod. Rep. 2014, 31, 504
15. Obora, Y.; Hatanaka, S.; Ishii, Y. Org. Lett. 2009, 11, 3510
16. Bower, J. F.; Skucas, E.; Patman, R. L.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 15134
17. Zbieg, J. R.; McInturff, E. L.; Leung, J. C.; Krische, M. J. J. Am. Chem. Soc. 2011, 133, 1141
18. Patman, R. L.; Chaulagain, M. R.; Williams, V. M.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 2066
19. Williams, V. M.; Leung, J. C.; Patman, R. L.; Krische, M. J. Tetrahedron 2009, 65, 5024
20. Leung, J. C.; Patman, R. L.; Sam, B.; Krische, M. J. Chem.-Eur. J. 2011, 17, 12437
21. Miura, T.; Nishida, Y.; Murakami, M. J. Am. Chem. Soc. 2014, 136, 6223
22. Miura, T.; Nishida, Y.; Morimoto, M.; Murakami, M. J. Am. Chem. Soc. 2013, 135, 11497
23. 2H, see: Zbieg, J. R.; Yamaguchi, E.; McInturff, E. L.; Krische, M. J. Science 2012, 336, 324 and ref 5b
24. 2,4,6-Tri(2-propyl)phenylsulfonic acid hydrate: Jautze, S.; Peters, R. Angew. Chem., Int. Ed. 2008, 47, 9284
25. 0, see: McInturff, E. L.; Mowat, J.; Waldeck, A. R.; Krische, M. J. J. Am. Chem. Soc. 2013, 135, 17230 and references cited therein
26. 1-allenyl complexes, see: Shuchart, C. E.; Willis, R. R.; Wojcicki, A. J. Organomet. Chem. 1992, 424, 185
27. For rhodium-catalyzed isomerization of 1-alkynes to allenes, see: Gellrich, U.; Meißner, A.; Steffani, A.; Kähny, M.; Drexler, H.-J.; Heller, D.; Plattner, D. A.; Breit, B. J. Am. Chem. Soc. 2014, 136, 1097
28. Wojcicki, A. Inorg. Chem. Commun. 2002, 5, 82
29. Xing, Y.; Wei, Y.; Zhou, H. Curr. Org. Chem. 2012, 16, 1594
30. Ogoshi, S.; Fukunishi, Y.; Tsutsumi, K.; Kurosawa, H. Inorg. Chim. Acta 1997, 265, 9 and references cited therein
31. Amarasinghe, K. K. D.; Montgomery, J. J. Am. Chem. Soc. 2002, 124, 9366
32. Montgomery, J.; Song, M. Org. Lett. 2002, 4, 4009
33. Kang, S.-K.; Yoon, S.-K. Chem. Commun. 2002, 2634
34. Takimoto, M.; Kawamura, M.; Mori, M. Org. Lett. 2003, 5, 2599
35. Takimoto, M.; Kawamura, M.; Mori, M. Synthesis 2004, 791
36. Song, M.; Montgomery, J. Tetrahedron 2005, 61, 11440
37. Ng, S.-S.; Jamison, T. F. J. Am. Chem. Soc. 2005, 127, 7320
38. Ng, S.-S.; Jamison, T. F. Tetrahedron 2005, 61, 11405
39. Ng, S.-S.; Jamison, T. F. Tetrahedron 2006, 62, 11350
40. For a computational study, see: Hratchian, H. P.; Chowdhury, S. K.; Gutiérrez-García, V. M.; Amarasinghe, K. K. D.; Heeg, M. J.; Schlegel, H. B.; Montgomery, J. Organometallics 2004, 23, 4636
41. Dewar, M. J. S. Bull. Soc. Chim. Fr. 1951, C71
42. Chatt, J.; Duncanson, L. A. J. Chem. Soc. 1953, 2939
43. Dewar, M. J. S.; Ford, G. P. J. Am. Chem. Soc. 1979, 101, 783
44. Yoshida, M.; Gotou, T.; Ihara, M. Tetrahedron Lett. 2003, 44, 7151
45. Bustelo, E.; Guérot, C.; Hercouet, A.; Carboni, B.; Toupet, L.; Dixneuf, P. H. J. Am. Chem. Soc. 2005, 127, 11582
46. Saito, S.; Dobashi, N.; Wakatsuki, Y. Chem. Lett. 2005, 34, 504
47. For palladium-catalyzed allene hydrodimerization, see: Oh, C. H.; Yoo, H. S.; Jung, S. H. Chem. Lett. 2001, 1288
48. Englert, M.; Jolly, P. W.; Wilke, G. Angew. Chem., Int. Ed. Engl. 1972, 11, 136
49. Pasto, D. J.; Huang, N.-Z.; Eigenbrot, C. W. J. Am. Chem. Soc. 1985, 107, 3160
50. Coulson, D. R. J. Org. Chem. 1973, 38, 1483
51. Arisawa, M.; Sugihara, T.; Yamaguchi, M. Chem. Commun. 1998, 2615
52. Saito, S.; Hirayama, K.; Kabuto, C.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 10776
53. Miura, T.; Biyajima, T.; Toyoshima, T.; Murakami, M. Beilstein J. Org. Chem. 2011, 7, 578
54. Li, X.-X.; Zhu, L.-L.; Zhou, W.; Chen, Z. Org. Lett. 2012, 14, 436
55. Jolly, P. W. Nickel Catalyzed Oligomerization of Alkynes and Related Reactions. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: Oxford, 1982; pp 664.
56. Schuster, H. F.; Coppola, G. M. Allenes in Organic Synthesis; Wiley: New York, 1984; Chapter 9, pp 286.
57. Pasto, D. J. Tetrahedron 1984, 40, 2805
58. Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Soc. Rev. 2010, 39, 783