Direct catalytic anti-markovnikov addition of carboxylic acids to alkenes

Journal of the American Chemical Society

Volumn 135, Issue 28, 2013, Pages 10334-10337

  Perkowski, Andrew J ^a   Nicewicz, David A ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST SYSTEM; ENAMIDES; POTENTIAL MECHANISM;

CARBOXYLIC ACIDS; STYRENE;

HYDROCARBONS;

ACRIDINE DERIVATIVE; ALIPHATIC CARBOXYLIC ACID; ALKENE; AMIDE; CARBOXYLIC ACID; DEUTERIUM; ENAMIDE DERIVATIVE; FUKUZUMI ACRIDINIUM; HYDROGEN; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ANTI MARKOVNIKOV ADDITION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; PHOTOOXIDATION; STOICHIOMETRY;

ACETATES; ALKENES; CARBOXYLIC ACIDS; CATALYSIS; MOLECULAR STRUCTURE;

EID: 84880392747     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja4057294     Document Type: Article

References (17)

1. Anderson, S. W.; Yates, K. Can. J. Chem. 1988, 66, 2412
2. Li, Z.; Zhang, J.; Brouwer, C.; Yang, C.; Reich, N. W.; He, C. Org. Lett. 2006, 8, 4175
3. Yang, C.; He, C. J. Am. Chem. Soc. 2005, 127, 6966
4. Yang, C.; Reich, N. W.; Shi, Z.; He, C. Org. Lett. 2005, 7, 4553
5. Choi, J.; Kohno, K.; Masuda, D.; Yasuda, H.; Sakakura, T. Chem. Commun. 2008, 777
6. Oe, Y.; Ohta, T.; Ito, Y. Chem. Commun. 2004, 1620
7. Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem., Int. Ed. 2004, 43, 3368
8. Shigemitsu, Y.; Arnold, D. R. J. Chem. Soc. Chem. Comm. 1975, 407
9. Gassman, P. G.; Bottorhoff, K. J. Tet. Lett. 1987, 28, 5449
10. Fukuzumi, S.; Kotani, H.; Ohkubo, K.; Ogo, S.; Tkachenko, N. V.; Lemmetyinen, H. J. Am. Chem. Soc. 2004, 126, 1600
11. Hamilton, D. S.; Nicewicz, D. A. J. Am. Chem. Soc. 2012, 134, 18577
12. Nguyen, T. M.; Nicewicz, D. A. J. Am. Chem. Soc. 2012, 10.1021/ja4031616
13. Grandjean, J. M.; Nicewicz, D. A. Angew. Chem., Int. Ed. 2013, 52, 3967
14. Wilger, D. J.; Gesmundo, N. J.; Nicewicz, D. A. Chem. Sci. 2013, 4, 3160
15. De Vleeschouwer, F.; Van Speybroech, V.; Waroquier, M.; Geerlings, P.; De Proft, F. Org. Lett. 2007, 7, 2721
16. Gersdorf, J.; Mattay, J.; Görner, H. J. Am. Chem. Soc. 1987, 109, 1203
17. 2-methyl-2-butene oxidation potential vs SCE: Patz, M.; Mayr, H.; Maruta, J.; Fukuzumi, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1225