O-H hydrogen bonding promotes H-atom transfer from α C-H bonds for C-alkylation of alcohols

Science

Volumn 349, Issue 6255, 2015, Pages 1532-1536

  Jeffrey, Jenna L ^a   Terrett, Jack A ^a   MacMillant, David W C ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID METHYL ESTER; ALCOHOL DERIVATIVE; ALKANOL; ALLYL COMPOUND; BENZILIC ACID; ETHER; HYDROGEN; HYDROXYL RADICAL; TETRA N BUTYLAMMONIUM PHOSPHATE; UNCLASSIFIED DRUG; CARBON; OXYGEN; QUATERNARY AMMONIUM DERIVATIVE; TETRABUTYLAMMONIUM;

ALCOHOL; CARBON; CATALYSIS; CHEMICAL BONDING; ETHER; HYDROGEN; KETONE; ORGANIC COMPOUND; OXYGEN; PHOSPHATE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CLINICAL EVALUATION; ELECTRON TRANSPORT; HYDROGEN BOND; KINETIC PARAMETERS; LACTONIZATION; NUCLEOPHILICITY; OXYGEN AFFINITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; CHEMISTRY;

ALCOHOLS; ALKYLATION; CARBON; CATALYSIS; HYDROGEN; HYDROGEN BONDING; OXYGEN; QUATERNARY AMMONIUM COMPOUNDS;

EID: 84942354069     PISSN: 00368075     EISSN: 10959203     Source Type: Journal    
DOI: 10.1126/science.aac8555     Document Type: Article

References (37)

1. D. Balcells, E. Clot, O. Eisenstein, Chem. Rev. 110, 749-823 (2010).
2. T. Newhouse, P. S. Baran, Angew. Chem. Int. Ed. 50, 3362-3374 (2011).
3. B. A. Arndtsen, R. G. Bergman, T. A. Mobley, T. H. Peterson, Acc. Chem. Res. 28, 154-162 (1995).
4. J. D. Lawrence, M. Takahashi, C. Bae, J. F. Hartwig, J. Am. Chem. Soc. 126, 15334-15335 (2004).
5. M. S. Chen, M. C. White, Science 327, 566-571 (2010).
6. E. A. Mader, E. R. Davidson, J. M. Mayer, J. Am. Chem. Soc. 129, 5153-5166 (2007).
7. J. J. Warren, J. M. Mayer, Proc. Natl. Acad. Sci. U. S. A. 107, 5282-5287 (2010).
8. J. M. Mayer, Acc. Chem. Res. 44, 36-46 (2011).
9. V. Paul, B. P. Roberts, J. Chem. Soc. Chem. Commun. (17):1322 (1987).
10. B. P. Roberts, Chem. Soc. Rev. 28, 25-35 (1999).
11. K. T. Tarantino, D. C. Miller, T. A. Callon, R. R. Knowles, J. Am. Chem. Soc. 137, 6440-6443 (2015).
12. F. G. Bordwell, J. A. Harrelson Jr., Can. J. Chem. 68, 1714-1718 (1990).
13. S. J. Blanksby, G. B. Ellison, Acc. Chem. Res. 36, 255-263 (2003).
14. L. J. J. Laarhoven, P. Mulder, D. D. M. Wayner, Acc. Chem. Res. 32, 342-349 (1999).
15. M. L. Steigerwald, W. A. Goddard III, D. A. Evans, J. Am. Chem. Soc. 101, 1994-1997 (1979).
16. D. A. Evans, D. J. Baillargeon, Tetrahedron Lett. 19, 3315-3318 (1978).
17. J. A. Cradlebaugh et al., Org. Biomol. Chem. 2, 2083-2086 (2004).
18. E. Gawlita et al., J. Am. Chem. Soc. 122, 11660-11669 (2000).
19. N. C. Maiti, Y. Zhu, I. Carmichael, A. S. Serianni, V. E. Anderson, J. Org. Chem. 71, 2878-2880 (2006).
20. U. Pal, S. Sen, N. C. Maiti, J. Phys. Chem. A 118, 1024-1030 (2014).
21. C. K. Prier, D. A. Rankic, D. W. C. MacMillan, Chem. Rev. 113, 5322-5363 (2013).
22. D. A. Nicewicz, D. W. C. MacMillan, Science 322, 77-80 (2008).
23. M. T. Pirnot, D. A. Rankic, D. B. C. Martin, D. W. C. MacMillan, Science 339, 1593-1596 (2013).
24. Z. Zuo et al., Science 345, 437-440 (2014).
25. K. Qvortrup, D. A. Rankic, D. W. C. MacMillan, J. Am. Chem. Soc. 136, 626-629 (2014).
26. D. Hager, D. W. C. MacMillan, J. Am. Chem. Soc. 136, 16986-16989 (2014).
27. J. Jin, D. W. C. MacMillan, Angew. Chem. Int. Ed. 54, 1565-1569 (2015).
28. J. D. Cuthbertson, D. W. C. MacMillan, Nature 519, 74-77 (2015).
29. F. Minisci, R. Galli, A. Galli, R. Bernardi, Tetrahedron Lett. 8, 2207-2209 (1967).
30. M. S. Lowry et al Chem Mater 17 5712-5719 (2005)
31. W.-Z. Liu, F. G. Bordwell, J. Org. Chem. 61, 4778-4783 (1996)
32. S. F. Nelsen, P. J. Hintz, J. Am. Chem. Soc. 94, 7114-7117 (1972).
33. M. A. Cismesia, T. P. Yoon, Chem. Sci. 6, 5426-5434 (2015).
34. M. Balci, Basic 1H-13C NMR Spectroscopy (Elsevier B. V., Amsterdam, 2005), pp. 325-332.
35. M. Newcomb, S. Y. Choi, Tetrahedron Lett. 34, 6363-6364 (1993).
36. S. Y. Choi, M. Newcomb, Tetrahedron 51, 657-664 (1995).
37. M. Newcomb, P. H. Toy, Acc. Chem. Res. 33, 449-455 (2000).