Pd-catalyzed aldehyde to ester conversion: A hydrogen transfer approach

Organic Letters

Volumn 15, Issue 3, 2013, Pages 500-503

  Tschaen, Brittany A ^a   Schmink, Jason R ^a,b   Molander, Gary A ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b BRYN MAWR COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ESTER; HYDROGEN; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; OXIDATION REDUCTION REACTION;

ALDEHYDES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; ESTERS; HYDROGEN; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PALLADIUM;

EID: 84873341132     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol303298g     Document Type: Article

References (29)

1. Otera, J.; Nishikido, J. Esterification. Methods, Reactions, and Applications, 2 nd ed.; Wiley-VCH: Weinheim, 2010.
2. Neises, B.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 522
3. Gopinath, R.; Patel, B. K. Org. Lett. 2000, 2, 577
4. Travis, B. R.; Sivakumar, M.; Hollist, G. O.; Borhan, B. Org. Lett. 2003, 5, 1031
5. Sayama, S.; Onami, T. Synlett 2004, 15, 2739
6. Maki, B. E.; Scheidt, K. A. Org. Lett. 2008, 10, 4331
7. Noonan, C.; Baragwanath, L.; Connon, S. J. Tetrahedron Lett. 2008, 49, 4003
8. Sarkar, S.; Grimme, S.; Studer, A. J. Am. Chem. Soc. 2010, 132, 1190
9. Reddy, R. S.; Rosa, J. N.; Veiros, L. F.; Caddick, S.; Gois, P. M. P. Org. Biomol. Chem. 2011, 9, 3126
10. Sohn, S. S.; Bode, J. W. Org. Lett. 2005, 7, 3873
11. Finney, E. E.; Ogawa, K. A.; Boydston, A. J. J. Am. Chem. Soc. 2012, 134, 12374
12. Kiyooka, S.; Ueno, M.; Ishii, E. Tetrahedron Lett. 2005, 46, 4639
13. Kiyooka, S.; Wada, Y.; Ueno, M.; Yokoyama, T.; Yokoyama, R. Tetrahedron 2007, 63, 12695
14. Grigg, R.; Mitchell, T.; Sutthivaiyakit, S. Tetrahedron 1981, 37, 4313
15. Murahashi, S.; Naota, T.; Ito, K.; Maeda, Y.; Taki, H. J. Org. Chem. 1987, 52, 4319
16. Heropoulos, G. A.; Villalonga-Barber, C. Tetrahedron Lett. 2011, 52, 5319
17. Liu, C.; Tang, S.; Zheng, L.; Liu, D.; Lei, A. Angew. Chem., Int. Ed. 2012, 51, 5662
18. Zhang, M.; Zhang, S.; Zhang, G.; Chen, F.; Cheng, J. Tetrahedron Lett. 2011, 52, 2480
19. Wolf, C.; Lerebours, R. J. Am. Chem. Soc. 2006, 128, 13052
20. Qin, C.; Wu, H.; Chen, J.; Liu, M.; Cheng, J.; Su, W.; Ding, J. Org. Lett. 2008, 10, 1537
21. Dreher, S. D.; Dormer, P. G.; Sandrock, D. L.; Molander, G. A. J. Am. Chem. Soc. 2008, 130, 9257
22. Almeida, M. L. S.; Beller, M.; Wamg, G.-Z.; Bäckvall, J.-E. Chem.-Eur. J. 1996, 2, 1533
23. Shue, R. S. Chem. Commun. 1971, 1510
24. Dams, M.; De Vos, D. E.; Celen, S.; Jacobs, P. A. Agnew. Chem., Int. Ed. 2003, 42, 3512
25. Wang, J.-R.; Yang, C.-T.; Liu, L.; Guo, Q.-X. Tetrahedron Lett. 2007, 48, 5449
26. Bäckvall, J. E.; Hopkins, R. B. Tetrahedron Lett. 1988, 29, 2885
27. Bäckvall, J. E.; Hopkins, R. B.; Grennberg, M. M.; Awasthi, A. K. J. Am. Chem. Soc. 1990, 112, 5160
28. Piera, J.; Bäckvall, J. E. Angew. Chem., Int. Ed. 2008, 47, 3506
29. Kinzel, T.; Zhang, Y.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 14073