Triethylborane-initiated radical chain fluorination: A synthetic method derived from mechanistic insight

Journal of Organic Chemistry

Volumn 79, Issue 18, 2014, Pages 8895-8899

  Pitts, Cody Ross ^a   Ling, Bill ^a   Woltornist, Ryan ^a   Liu, Ran ^a   Lectka, Thomas ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHAINS; FLUORINE; HALOGENATION;

INDUSTRIAL PROCESSS; MECHANISTIC STUDIES; RADICAL CHAIN; RADICAL INITIATORS; SELECTFLUOR; SYNTHETIC METHODS; TRIETHYLBORANE;

FLUORINATION;

BORANE DERIVATIVE; COPPER; CUPROUS ION; CYCLODECANE; OXYGEN; RADICAL; TRIETHYLBORANE; UNCLASSIFIED DRUG;

ARTICLE; AUTOOXIDATION; ELECTRON TRANSPORT; FLUORINATION; REACTION TIME; ROOM TEMPERATURE; SYNTHESIS;

EID: 84911889860     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501520e     Document Type: Article

References (29)

1. Pitts, C. R.; Bloom, S.; Woltornist, R.; Auvenshine, D.; Ryzhkov, L. R.; Siegler, M. A.; Lectka, T. J. Am. Chem. Soc. 2014, 136, 9780-9791.
2. For a fairly comprehensive introduction to radical initiators, see: Denisov, E. T.; Denisova, T. G.; Pokidova, T. S. Handbook of Free Radical Initiators; Wiley: Hoboken, NJ, 2003.
3. Ollivier, C.; Renaud, P. Chem. Rev. 2001, 101, 3415-3434 and references cited therein.
4. Brotherton, R. J.; Weber, C. J.; Guibert, C. R.; Little, J. L. Boron Compounds. In Ullman's Encyclopedia in Industrial Chemistry; Wiley-VCH: Weinheim, Germany, 2000
5. Rueda-Becerril, M.; Sazepin, C. C.; Leung, J. C. T.; Okbinoglu, T.; Kennepohl, P.; Paquin, J.-F.; Sammis, G. M. J. Am. Chem. Soc. 2012, 134, 4026-4029.
6. Amaoka, Y.; Nagatomo, M.; Inoue, M. Org. Lett. 2013, 15, 2160-2163.
7. Xia, J.-B.; Ma, Y.; Chen, C. Org. Chem. Front. 2014, 1, 468-472.
8. However, some of these photochemical approaches may be operating very differently mechanistically. For some examples, see: (a) Bloom, S.; Knippel, J. L.; Lectka, T. Chem. Sci. 2014, 5, 1175-1178.
9. (b) Kee, C. W.; Chin, K. F.; Wong, M. W.; Tan, C.-H. Chem. Commun. 2014, 50, 8211-8214.
10. (c) Xia, J.-B.; Zhu, C.; Chen, C. J. Am. Chem. Soc. 2013, 135, 17494-17500.
11. (a) Bertrand, M. P.; Feray, L.; Nouguier, R.; Perfetti, P. J. Org. Chem. 1999, 64, 9189-9193.
12. (b) Ryu, I.; Araki, F.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1998, 39, 6335-6336.
13. Achord, J. M.; Hussey, C. L. Anal. Chem. 1980, 52, 601-602.
14. Tanuma, T.; Ohnishi, K.; Okamoto, H.; Morikawa, S. J. Fluorine Chem. 1996, 76, 45-48.
15. Zhang, Z.-C.; Chung, T. C. M. Macromolecules 2006, 39, 5187-5189.
16. (a) Byers, J. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, p 72.
17. (b) Curran, D. P.; Chen, M.-H.; Spetzler, E.; Seong, C. M.; Chang, C.-T. J. Am. Chem. Soc. 1989, 111, 8872-8878.
18. Frisch, M. J., et al. Gaussian 09, Revision A.1; Gaussian, Inc., Wallingford, CT, 2009.
19. Bernardi, R.; Galli, R.; Minisci, F. J. Chem. Soc. B 1968, 324-325.
20. For example, see: Xia, J.-B.; Ma, Y.; Chen, C. Org. Chem. Front. 2014, 1, 468-472.
21. Similar site selectivity was observed on the same substrate by Groves et al. in a different approach to sp C-H fluorination: Liu, W.; Huang, X.; Cheng, M.-J.; Nielsen, R. J.; Goddard, W. A., III; Groves, J. T. Science 2012, 337, 1322-1325.
22. See discussion and references in: Bloom, S.; Pitts, C. R.; Woltornist, R.; Griswold, A.; Holl, M. G.; Lectka, T. Org. Lett. 2013, 15, 1722-1724.
23. Naumann, D.; Kischkewitz, J. J. Fluorine Chem. 1990, 47, 283-299.
24. Schneider, H.-J.; Gschwendtner, W.; Heiske, D.; Hoppen, V.; Thomas, F. Tetrahedron 1977, 33, 1769-1773.
25. Beaulieu, F.; Beauregard, L.; Courchesne, G.; Couturier, M.; La Flamme, F.; L'Heureux, A. Org. Lett. 2009, 11, 5050-5053.
26. Aoyama, M.; Fukuhara, T.; Hara, S. J. Org. Chem. 2008, 73, 4186-4189.
27. York, C.; Prakash, G. K. S.; Olah, G. A. Tetrahedron 1996, 52, 9-14.
28. Bloom, S.; Sharber, S. A.; Holl, M. G.; Knippel, J. L.; Lectka, T. J. Org. Chem. 2013, 78, 11082-11086.
29. ACD/NMR Processor Academic ed., version 12.0; Advanced Chemistry Development, Inc., Toronto, ON, Canada, 2012; www.acdlabs.com.