Preparative synthesis via continuous flow of 4,4,5,5-tetramethyl-2-(3- trimethylsilyl-2-propynyl)-1,3,2-dioxaborolane: A general propargylation reagent

Organic Process Research and Development

Volumn 16, Issue 5, 2012, Pages 1131-1140

  Fandrick, Daniel R ^a   Roschangar, Frank ^a   Kim, Chunyoung ^b   Hahm, Byoung J ^b   Cha, Myoung H ^b   Kim, Hyoun Y ^b   Yoo, Gyesang ^b   Kim, Taeyun ^b   Reeves, Jonathan T ^a   Song, Jinhua J ^a   Tan, Zhulin ^a   Qu, Bo ^a   Haddad, Nizar ^a   Shen, Sherry ^a   Grinberg, Nelu ^a   Lee, Heewon ^a   Yee, Nathan ^a   Senanayake, Chris H ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

^b SK Holdings ^*  (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

BATCH PROCESS; CONTINUOUS FLOWS; CONTINUOUS-FLOW; DISTILLATION PROCESS; N-BUTYLLITHIUM; PINACOLS; PROPARGYLATION; PROTONOLYSIS;

DISTILLATION;

BATCH DATA PROCESSING;

EID: 84862060346     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op200180t     Document Type: Article

References (38)

1. Hall, D. G. Boronic Acids; Wiley-VCH: Weinheim, Germany, 2005.
2. Fandrick, D. R.; Reeves, J. T.; Song, J. J. Process for Stereoselective Synthesis of Alkynyl Aryl Trifluoromethyl Alcohols via Reaction of Silylalkynylborolanes with Trifluoromethyl Ketones. PCT Int. Appl. WO/2010/141328, 2010.
3. Fandrick, D. R.; Fandrick, K. R.; Reeves, J. T.; Tan, Z.; Johnson, C. S.; Lee, H.; Song, J. J.; Yee, N. K.; Senanayake, C. H. Org. Lett. 2010, 12, 88-91
4. Fandrick, D. R.; Johnson, C. S.; Fandrick, K. R.; Reeves, J. T.; Tan, Z.; Lee, H.; Song, J. J.; Yee, N. K.; Senanayake, C. H. Org. Lett. 2010, 12, 748-751
5. Fandrick, D. R.; Fandrick, K. R.; Reeves, J. T.; Tan, Z.; Tang, W.; Capacci, A. G.; Rodriguez, S.; Song, J. J.; Lee, H.; Yee, N. K.; Senanayake, C. H. J. Am. Chem. Soc. 2010, 132, 7600-7601
6. Fandrick, K. F.; Fandrick, D. R.; Reeves, J. T.; Gao, J.; Ma, S.; Li, W.; Lee, H.; Grinberg, N.; Lu, B.; Senanayake, C. H. J. Am. Chem. Soc. 2011, 137, 10332-10335
7. Fandrick, D. R.; Reeves, J. T.; Tan, Z.; Lee, H.; Song, J. J.; Yee, N. K.; Senanayake, C. H. Org. Lett. 2009, 11, 5458-5461
8. Knochel, P.; Ila, H.; Korn, T. J.; Baron, O. Functionalized Organoborane Derivatives in Organic Synthesis. In Handbook of Functionalized Organometallics; Knochel, P., Ed.; Wiley-VCH: Weinheim, 2005; Vol 1, Chapter 3.
9. Hoffmann, R. W.; Brinkmann, H.; Frenking, G. Chem. Ber. 1990, 123, 2387-2394
10. Blais, J.; L'Honore, A.; Soulie, J.; Cadiot, P. J. Organomet. Chem. 1974, 78, 323-337
11. Coffee, R. D.; Wheeler, J. J. Loss Prev. 1967, 1, 6-9
12. Magin, R. W.; Herndon, R. C.; Sabahi, M.; Allen, R. H.; Brantley, N. H.; Elnagar, H. Y.; Lin, R. W. Stabilized Propargyl Bromide Compositions as Soil Fumigants. U.S. Pat. Appl. Publ. U.S. 20030194514, 2003.
13. Sabahi, M.; Magin, R. W.; Herndon, R. C.; Elnagar, H. Y.; Brantley, N. H.; Lin, R. W.; Allen, R. H. Stabilization and Use of Propargyl Bromide, U.S. Pat. Appl. Publ. U.S. 2003087024, 2003.
14. Orsini, F.; Pelizzoni, F. Synth. Commun. 1984, 14, 805-816
15. Orsini, F. Synthesis 1985, 500-503
16. Verkruijsse, H. D.; Brandsma, L. Synth. Commun. 1990, 20, 3375-3378
17. Trost, B. M.; Huang, X. Chem.-Asian J. 2006, 1, 469-478
18. Chen, D.-D.; Hou, X.-L.; Dai, L.-X. Tetrahedron Lett. 2009, 50, 6944-6946
19. MacInnes, I.; Walton, J. C. J. Chem. Soc., Perkin Trans. 2 1987, 1077-1082
20. Yao, G.; Steliou, K. Org. Lett. 2002, 4, 485-488
21. Banerjee, M.; Roy, S. Org. Lett. 2004, 6, 2137-2140
22. Schelper, M.; De Meijere, A. Eur. J. Org. Chem. 2005, 582-592
23. Bernard, S.; Defoy, D.; Dory, Y. L.; Klarskov, K. Bioorg. Med. Chem. Lett. 2009, 19, 6127-6130
24. Zweifel, G.; Pearson, N. R. J. Org. Chem. 1981, 46, 829-830
25. Soundararajan, R.; Li, G.; Brown, H. C. Tetrahedron Lett. 1994, 35, 8961-8964
26. Brown, H. C.; Roy, C. D.; Soundararajan, R. Tetrahedron Lett. 1997, 38, 765-768
27. Corey, E. J.; Kirst, H. A. Tetrahedron Lett. 1968, 9, 5041-5043
28. Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366
29. Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377
30. Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131
31. Hernandez, E.; Soderquist, J. A. Org. Lett. 2005, 7, 5397-5400
32. Hernandez, E.; Burgos, C. H.; Alicea, E.; Soderquist, J. A. Org. Lett. 2006, 8, 4089-4091
33. Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L. J. Am. Chem. Soc. 1999, 121, 9769-9780
34. Anderson, N. G. Practical Process Research & Development; Academic Press: San Diego, 2000; Chapters 1 and 13.
35. Brown, H. C.; Cole, T. E. Organometallics 1985, 4, 816-821
36. Brown, H. C.; Srebnik, M.; Cole, T. E. Organometallics 1986, 5, 2300-2303
37. Raushel, J.; Sandrock, D. L.; Josyula, K. V.; Pakyz, D.; Molander, G. A. J. Org. Chem. 2011, 76, 2762-2769
38. Brown, H. C.; Cole, T. E. Organometallics 1983, 2, 1316-1319