Palladium(II)-catalyzed aerobic dialkoxylation of styrenes: A profound influence of an o-phenol

Journal of the American Chemical Society

Volumn 128, Issue 5, 2006, Pages 1460-1461

  Schultz, Mitchell J ^a   Sigman, Matthew S ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; PHENOL; STYRENE;

ALKYLATION; ARTICLE; CATALYSIS; DECOMPOSITION; ISOMERISM; OXIDATIVE STRESS; REACTION ANALYSIS; REACTION OPTIMIZATION; STEREOCHEMISTRY;

ALKYLATION; CATALYSIS; OXIDATION-REDUCTION; OXYGEN; PALLADIUM; PHENOLS; STEREOISOMERISM; STYRENES;

EID: 32244442435     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0579053     Document Type: Article

References (17)

1. For a review, see: Netherton, M. R.; Fu, G. C. In Topics in Organometallic Chemistry: Palladium in Organic Synthesis: Tsuji, J., Ed.; Springer-Verlag: Germany: 2005; pp 85-108.
2. For recent reviews of Pd-catalyzed oxidations, see: (a) Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400-3420.
3. (b) Sigman, M. S.; Schultz, M. J. Org. Biomol. Chem. 2004, 2, 2551-2554.
4. It has been reported that allyl phenol isomerizes under similar conditions, see: Gross, J. L. Tetrahedron Lett. 2003, 44, 8563-8565.
5. Byproducts of this reaction resulted from Wacker-type cyclbations.
6. Recently, two reports have appeared on Pd-catalyzed diamination of olefins: (a) Streuff, J.; Hövelmann, C. H.; Nieger, M.; Muñiz, K. J. Am. Chem. Soc. 2005, 127, 14586-14587.
7. (b) Bar, G. L. J.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. J. Am. Chem. Soc. 2005, 127, 7308-7309.
8. The relative stereochemistry was assigned by comparison to an independently prepared syn product. The diastereomeric ratio was measured via 1H NMR. See Supporting Information for details.
9. Hosokawa, T.; Ohta, T.; Kanayama, S.; Murahashi, S.-I. J. Org. Chem. 1987, 52, 1758-1764.
10. For a review on quinone methides, see: Van de Water, R. W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367-5405.
11. Chapman has reported methanol attacking a similar quinone methide, see: Chapman, O. L.; McIntosh, C. L. Chem. Commun. 1971, 383-384.
12. Chapman, O. L.; Engel, M. R.; Springer, J. P.; Clardy, J. C. J. Am. Chem. Soc. 1971, 93, 6696-6698.
13. For a recent example, see: Dick, A. R.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 12790-12791 and references therein.
14. Evaluation of a p-phenol did not lead to product but instead to significant substrate and catalyst decomposition.
15. For examples of a similar cyclic acetal formation, see: (a) Hosokawa, T.; Nakajima, F.; Iwasa, S.; Murahashi, S.-I. Chem. Lett. 1990, 1387-1390.
16. (b) Igarashi, S.; Haruta, Y.; Ozawa, M.; Nishide, Y.; Kinoshita, H.; Inomata, K. Chem. Lett. 1989, 737-740.
17. For similar observed diastereomeric ratios in Michael-type reactions, see: Yamamoto, Y.; Chounan, Y.; Nishii, S.; Ibuka, T.; Kitahara, H. J. Am. Chem. Soc. 1992, 114, 7652-7660.