Palladium-catalyzed intermolecular aminoacetoxylation of alkenes and the influence of PhI(OAc)2 on aminopalladation stereoselectivity

Journal of Organic Chemistry

Volumn 78, Issue 12, 2013, Pages 6309-6315

  Martínez, Claudio ^a   Wu, Yichen ^b   Weinstein, Adam B ^c   Stahl, Shannon S ^c   Liu, Guosheng ^b   Muñiz, Kilian ^a,d  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c UNIVERSITY OF WISCONSIN MADISON   (United States)

^d INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AEROBIC CONDITION; CRYSTALLOGRAPHIC CHARACTERIZATION; DIACETOXYIODOBENZENE; ISOTOPIC LABELING; PALLADIUM-CATALYZED;

CATALYSIS; X RAY CRYSTALLOGRAPHY;

HYDROCARBONS;

ALKENE; BENZENE DERIVATIVE; IODINE; PALLADIUM;

AMIDATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; INTERMOLECULAR AMINOACETOXYLATION; ISOMER; ISOTOPE LABELING; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

ALKENES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; DEUTERIUM; IODOBENZENES; ISOTOPE LABELING; MOLECULAR STRUCTURE; OXYGEN; PALLADIUM; STEREOISOMERISM;

EID: 84879375632     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400671q     Document Type: Article

References (45)

1. Alexanian, E. J.; Lee, C.; Sorensen, E. J. J. Am. Chem. Soc. 2005, 127, 7690-7691
2. Liu, G.; Stahl, S. S. J. Am. Chem. Soc. 2006, 128, 7179-7181
3. For a related aminoetherification reaction, see: Desai, L. V.; Sanford, M. S. Angew. Chem., Int. Ed. 2007, 46, 5737-5740
4. Iglesias, á.; Pérez, E. G.; Muñiz, K. Angew. Chem., Int. Ed. 2010, 49, 8109-8111
5. Muñiz, K.; Kirsch, J.; Chávez, P. Adv. Synth. Catal. 2011, 353, 689-694
6. Martínez, C.; Muñiz, K. Angew. Chem., Int. Ed. 2012, 51, 7031-7034
7. Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285-2309
8. Beccali, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318-5365
9. Minatti, A.; Muñiz, K. Chem. Soc. Rev. 2007, 36, 1142-1152
10. Kotov, V.; Scarborough, C. C.; Stahl, S. S. Inorg. Chem. 2007, 46, 1910-1923
11. Jensen, K. H.; Sigman, M. S. Org. Biomol. Chem. 2008, 6, 4083-4088
12. McDonald, R. I.; Liu, G.; Stahl, S. S. Chem. Rev. 2011, 111, 2981-3019
13. Canty, A. J.; Denney, M. C.; Skelton, B. W.; White, A. H. Organometallics 2004, 23, 1122-1131
14. Dick, A. R.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 12790-12791
15. Powers, D. C.; Ritter, T. Nat. Chem. 2009, 1, 302-309
16. Deprez, N. R.; Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 11234-11241
17. Powers, D. C.; Lee, E.; Ariafard, A.; Sanford, M. S.; Yates, B. F.; Canty, A. J.; Ritter, T. J. Am. Chem. Soc. 2012, 134, 12002-12009
18. Powers, D. C.; Ritter, T. Acc. Chem. Res. 2012, 45, 840-850
19. Muñiz, K. Angew. Chem., Int. Ed. 2009, 48, 9412-9423
20. Hickman, A. J.; Sanford, M. S. Nature 2012, 484, 177-185
21. Fles, D.; Majhofer, B.; Kovac, M. Tetrahedron 1968, 24, 3053-3057
22. Sibbald, P. A.; Rosewall, C. F.; Swartz, R. D.; Michael, F. E. J. Am. Chem. Soc. 2009, 131, 15945-15951
23. Iglesias, á.; álvarez, R.; de Lera, á. R.; Muñiz, K. Angew. Chem., Int. Ed. 2012, 51, 2225-2228
24. Williams, B. S.; Goldberg, K. I. J. Am. Chem. Soc. 2001, 123, 2576-2587
25. Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2182-2192 and references therein
26. Byers, P. K.; Canty, A. J.; Crespo, M.; Puddephatt, R. J.; Scott, J. D. Organometallics 1988, 7, 1363-1367
27. Coulson, D. R. J. Am. Chem. Soc. 1969, 91, 200-202
28. Wong, P. K.; Stille, J. K. J. Organomet. Chem. 1974, 70, 121-132
29. Bäckvall, J.-E. Tetrahedron Lett. 1977, 18, 467-468
30. Bäckvall, J.-E. Tetrahedron Lett. 1978, 19, 163-166
31. Zhu, G.; Ma, S.; Lu, X.; Huang, Q. J. Chem. Soc., Chem. Commun. 1995, 271-273
32. Desai, L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542-9543
33. IV, see: Khusnutdinova, J. R.; Newman, L. L.; Zavalij, P. Y.; Lam, Y. F.; Vedernikov, A. N. J. Am. Chem. Soc. 2008, 130, 2174-2175
34. Nakhla, J. S.; Kampf, J. W.; Wolfe, J. P. J. Am. Chem. Soc. 2006, 128, 2893-2901
35. Liu, G.; Stahl, S. S. J. Am. Chem. Soc. 2007, 129, 6328-6335
36. Keith, J. A.; Henry, P. M. Angew. Chem., Int. Ed. 2009, 48, 9038-9049
37. Weinstein, A. B.; Stahl, S. S. Angew. Chem., Int. Ed. 2012, 51, 11505-11509
38. Ye, X.; Liu, G.; Popp, B. V.; Stahl, S. S. J. Org. Chem. 2011, 76, 1031-1044
39. Ye, X.; White, P. B.; Stahl, S. S. J. Org. Chem. 2013, 78, 2083-2090
40. Hadjiarapoglou, L.; Spyroudis, S.; Varvoglis, A. Synthesis 1983, 207-208
41. Kim, H. J.; Kim, J.; Cho, S. H.; Chang, S. J. Am. Chem. Soc. 2011, 133, 16382-16385
42. Moriyama, K.; Ishida, K.; Togo, H. Org. Lett. 2012, 14, 946-949
43. Yagi, K.; Oikawa, H.; Ichihara, A. Biosci., Biotechnol., Biochem. 1997, 61, 1038-1040
44. Product 4 is a known compound: Rogers, M. M.; Kotov, V.; Chatwichien, J.; Stahl, S. S. Org. Lett. 2007, 9, 4331-4334
45. 1H NMR was consistent with the data in the literature: Bégis, G.; Cladingboel, D. E.; Jerome, L.; Motherwell, W. B.; Sheppard, T. D. Eur. J. Org. Chem. 2009, 1532-1548