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Kevin S. Williamson Yoon Group April 9, 2009

Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

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Page 1: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

Kevin S. Williamson

Yoon Group

April 9, 2009

Page 2: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

2

Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163

US Patent 2230654

Page 3: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 3

Page 4: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

4Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163

O’Hagan et al. Nature 2004, 427, 561-565

Page 5: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

5Fried, J.H.; Sabo, E.F. JACS 1953, 75, 2273-74Fried, J.H.; Sabo, E.F. JACS 1954, 76, 1455-56

Page 6: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

6H.-J. Böhm et al. ChemBioChem 2004, 5, 637-643Kirk, K.L. Organic Process Research and Development 2008, 12, 305-321

Page 7: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

7H.-J. Böhm et al. ChemBioChem 2004, 5, 637-643M.A. Massa et al. Bioorganic and Medicinal Chemistry Letters 2001, 11, 1625-28

Page 8: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

8H.-J. Böhm et al. ChemBioChem 2004, 5, 637-643

Page 9: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

9

R = H R = F H.-J. Böhm et al. ChemBioChem 2004, 5, 637-643Boehm et al. J. Med. Chem. 1996, 39, 3929-3937

Page 10: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

10Purrington, S.T.; Woodard, D.L. JOC 1991, 56, 142Wong et al. ACIE 2005, 44, 192-212

NaF(s) KI traps5% F2 in N2

N2

REACTOR

Tygon & Teflon

Tubing

Page 11: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

11Wong et al. ACIE 2005, 44, 192-212R.E. Banks, US Patent 5,086,178

Page 12: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

12Differding, E.; Lang, R.W.; TL 1988, 29, 6087-6090

Page 13: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

13Shibata, N.; Suzuki, E; Takeuchi, Y. JACS 2000, 122, 10728-10729

Page 14: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

14Hintermann, L.; Togni, A. ACIE 2000, 39, 4359-4362

Page 15: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

15Shibata et al. ACIE 2005, 44, 4204-4207

Page 16: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

16Beeson, T.D.; MacMillan, D.W.C.; JACS 2005, 127, 8826-8828

Steiner, D.D; Mase, N.; Barbas III, C.F.; ACIE 2005, 44, 3706-3710

Page 17: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

17Jørgensen et al. ACIE 2005, 44, 3703-3706

Page 18: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

18Jørgensen et al. ACIE 2005, 44, 3703-3706

Page 19: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

19Jørgensen et al. ACIE 2005, 44, 3703-3706

Page 20: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

20Bruns, S.; Haufe, G. Journal of Fluorine Chemistry 2000, 104, 247-254

Togni et al. Eur. J. Inorg. Chem. 2006, 1397-1412

Page 21: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

21Ferraris, J.P.; Saito, G. J. Chem. Soc. Chem. Commun. 1979, 914

Suzuki, H.; Kimura, Y. J. Fluorine Chem. 1991, 52, 341-351

Page 22: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

22Hull, K.L.; Anani, W.Q.; Sanford, M.S. JACS 2006, 128, 7134-7135

Page 23: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

23Ball, N.D.; Sanford, M.S. JACS 2009, 131, 3796-97

Page 24: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

24Ball, N.D.; Sanford, M.S. JACS 2009, 131, 3796-97

Page 25: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

25Furuya, T.; Kaiser, H.M.; Ritter, R. ACIE 2008, 47, 5993-5996

Page 26: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

26Furuya, T.; Ritter, T. JACS 2008, 130, 10060-10061

Page 27: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

27Furuya, T.; Strom, A.; Ritter, T. JACS 2009, 131, 1662-1663

Page 28: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

28Furuya, T.; Strom, A.; Ritter, T. JACS 2009, 131, 1662-1663

Page 29: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

29Phelps, M.E. PNAS 2000, 97, 9226-9233

Page 30: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654

30Phelps, M.E. PNAS 2000, 97, 9226-9233

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Page 33: Kevin S. Williamson Yoon Group April 9, 2009. 2 Dolbier Jr., W.R. Journal of Fluorine Chemistry 2005, 126, 157-163 US Patent 2230654