Engaging unactivated alkyl, alkenyl and aryl iodides in visible-light-mediated free radical reactions

Nature Chemistry

Volumn 4, Issue 10, 2012, Pages 854-859

  Nguyen, John D ^a   D'Amato, Erica M ^a   Narayanam, Jagan M R ^a   Stephenson, Corey R J ^a  

^a Boston University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; FREE RADICAL; HYDROGEN; IODIDE;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; LIGHT; OXIDATION REDUCTION REACTION;

CARBON; CATALYSIS; CYCLIZATION; FREE RADICALS; HYDROGEN; IODIDES; LIGHT; OXIDATION-REDUCTION;

EID: 84866890642     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.1452     Document Type: Article

References (48)

1. Alonso, F., Beletskaya, I. P. & Yus, M. Metal-mediated reductive hydrodehalogenation of organic halides. Chem. Rev. 102, 4009-4091 (2002).
2. Bailey, W. F. & Patricia, J. J. The mechanism of the lithium halogen interchange reaction-a review of the literature. J. Organomet. Chem. 352, 1-46 (1988).
3. Knochel, P. et al. Highly functionalized organomagnesium reagents prepared through halogen-metal exchange. Angew. Chem. Int. Ed. 42, 4302-4320 (2003).
4. Yoon, N. M. Selective reduction of organic compounds with aluminum and boron hydrides. Pure Appl. Chem. 68, 843-848 (1996).
5. Chen, J. et al. A practical palladium catalyzed dehalogenation of aryl halides and a-haloketones. Tetrahedron 63, 4266-4270 (2007).
6. Curran, D. P. & Rakiewicz, D. M. Tandem radical approach to linear condensed cyclopentanoids. Total synthesis of (+)-hirsutene. J. Am. Chem. Soc. 107, 1448-1449 (1985).
7. Depew, K. M. et al. Total synthesis of 5-N-acetylardeemin and amauromine: practical routes to potential MDR reversal agents. J. Am. Chem. Soc. 121, 11953-11963 (1999).
8. Kim, J., Ashenhurst, J. A. & Movassaghi, M. Total synthesis of ()-11,11′- dideoxyverticillin A. Science 324, 238-241 (2009).
9. Neumann,W. P. Tri-n-butyltin hydride as reagent in organic synthesis. Synthesis 665-683 (1987).
10. Sanchez, J. & Myers, T. N. Kirk-Othmer Encyclopedia of Chemical Technology 4th edn, 431-460 (Wiley, 2000).
11. Krief, A. & Laval, A-M. Coupling of organic halides with carbonyl compounds promoted by SmI2, the Kagan reagent. Chem. Rev. 99, 745-777 (1999).
12. Miura, K. et al. Triethylborane-induced hydrodehalogenation of organic halides by tin hydrides. Bull. Chem. Soc. Jpn 62, 143-147 (1989).
13. Medeiros, M. R., Schacherer, L. N., Spiegel, D. A. & Wood, J. L. Expanding the scope of trialkylborane/water-mediated radical reactions. Org. Lett. 9, 4427-4429 (2007).
14. Murphy, J. A., Khan, T. A., Zhou, S. Z., Thomson, D. W. & Mahesh, M. Highly efficient reduction of unactivated aryl and alkyl iodides by a ground-state neutral organic electron donor. Angew. Chem. Int. Ed. 44, 1356-1360 (2005).
15. Cahard, E. et al. Electron transfer to benzenes by photoactivated neutral organic electron donor molecules. Angew. Chem. Int. Ed. 51, 3673-3676 (2012).
16. Weiss, M. E., Kreis, L. M., Lauber, A. & Carreira E. M. Cobalt-catalyzed coupling of alkyl iodides with alkenes: deprotonation of hydridocobalt enables turnover. Angew. Chem. Int. Ed. 50, 11125-11128 (2011).
17. Ueng, S. H., Fensterbank, L., Lacôte, E., Malacria, M. & Curran, D. P. Radical reductions of alkyl halides bearing electron withdrawing groups with N-heterocyclic carbene boranes. Org. Biomol. Chem. 9, 3415-3420 (2011).
18. Spiegel, D. A., Wiberg, K. B., Schacherer, L. N., Medeiros, M. R. & Wood, J. L. Deoxygenation of alcohols employing water as the hydrogen atom source. J. Am. Chem. Soc. 127, 12513-12515 (2005).
19. Gansaüer, A. et al. H2O activation for hydrogen-atom transfer: correct structures and revised mechanisms. Angew. Chem. Int. Ed. 51, 3266-3270 (2012).
20. Neumann, M., Füldner, S., König, B. & Zeitler, K. Metal-free, cooperative asymmetric organophotoredox catalysis with visible light. Angew. Chem. Int. Ed. 50, 951-954 (2011).
21. Narayanam, J. M. R. & Stephenson, C. R. J. Visible light photoredox catalysis: applications in organic synthesis. Chem. Soc. Rev. 40, 102-113 (2011).
22. Furst, L., Narayanam, J. M. R. & Stephenson, C. R. J. Total synthesis of ()-gliocladin C enabled by visible light photoredox catalysis. Angew. Chem. Int. Ed. 50, 9655-9659 (2011).
23. Tucker, J.W., Narayanam, J.M. R., Krabbe, S.W. & Stephenson, C. R. J. Electron transfer photoredox catalysis: intramolecular radical addition to indoles and pyrroles. Org. Lett. 12, 368-371 (2010).
24. Furst, L.,Matsuura, B. S., Narayanam, J.M. R., Tucker, J.W. & Stephenson, C. R. J. Visible light-mediated intermolecular C-H functionalization of electron-rich heterocycles with malonates. Org. Lett. 12, 3104-3107 (2010).
25. Nguyen, J. D., Tucker, J. W., Konieczynska, M. D. & Stephenson, C. R. J. Intermolecular atom transfer radical addition to olefins mediated by oxidative quenching of photoredox catalysts. J. Am. Chem. Soc. 133, 4160-4163 (2011).
26. Nagib, D. A., Scott, M. E. & MacMillan, D. W. C. Enantioselective a-trifluoromethylation of aldehydes via photoredox organocatalysis. J. Am. Chem. Soc. 131, 10875-10877 (2009).
27. Dai, C., Narayanam, J. M. R. & Stephenson, C. R. J. Visible light mediated conversion of alcohols to halides. Nature Chem. 3, 140-145 (2011).
28. Freeman, D. B., Furst, L., Condie, A. G. & Stephenson, C. R. J. Functionally diverse nucleophilic trapping of iminium intermediates generated utilizing visible light. Org. Lett. 14, 94-97 (2012).
29. Shih, H. W., Vander Wal, M. N., Grange, R. L. & MacMillan, D. W. C. Enantioselective a-benzylation of aldehydes via photoredox organocatalysis. J. Am. Chem. Soc. 132, 13600-13603 (2010).
30. Nicewicz, D. A. & MacMillan D. W. C. Merging photoredox catalysis with organocatalysis: the direct asymmetric alkylation of aldehydes. Science 322, 77-80 (2008).
31. Tucker, J. W. & Stephenson, C. R. J. Tandem visible light-mediated radical cyclization-divinylcyclopropane rearrangement to tricyclic pyrrolidinones. Org. Lett. 13, 5468-5471 (2011).
32. Andrews, R. S., Becker, J. J. & Gagné, M. R. Intermolecular addition of glycosyl halides to alkenes mediated by visible light. Angew. Chem. Int. Ed. 49, 7274-7276 (2010).
33. Lowry, M. S. et al. Single-layer electroluminescent devices and photoinduced hydrogen production from an ionic iridium(III) complex. Chem. Mater. 17, 5712-5719 (2005).
34. Juris, A. et al. Ru(II) polypyridine complexes: photophysics, photochemistry, electrochemistry, and chemiluminescence. Coord. Chem. Rev. 84, 85-277 (1988).
35. Flamigni, L., Barbieri, A., Sabatini, C., Ventura, B. & Barigelletti, F. Photochemistry and photophysics of coordination compounds: iridium. Top. Curr. Chem. 281, 143-203 (2007).
36. Dixon, I. M. et al. A family of luminescent coordination compounds: iridium(III) polyimine complexes. Chem. Soc. Rev. 29, 385-391 (2000).
37. Tucker, J.W. & Stephenson, C. R. J. Shining light on photoredox catalysis: theory and synthetic applications. J. Org. Chem. 77, 1617-1622 (2012).
38. Tucker, J. W., Nguyen, J. D., Narayanam, J. M. R., Krabbe, S. W. & Stephenson, C. R. J. Tin-free radical cyclization reactions initiated by photoredox catalysis. Chem. Commun. 46, 4985-4987 (2010).
39. Wallentin, C-J., Nguyen, J. D., Finkbeiner, P. & Stephenson, C. R. J. Visible lightmediated atom transfer radical addition via oxidative and reductive quenching of photocatalysts. J. Am. Chem. Soc. 134, 8875-8884 (2012).
40. Hill, H. A. O., Pratt, J. M., O'Riordan, M. P., Williams, F. R. & Williams, R. J. P. The chemistry of vitamin B12. Part XV. Catalysis of alkyl halide reduction by vitamin B12a: studies using controlled potential reduction. J. Chem. Soc. A 1859-1862 (1971).
41. Rondinini, S., Mussini, P. R., Muttini, P. & Sello, G. Silver as a powerful electrocatalyst for organic halide reduction: the critical role of molecular structure. Electrochim. Acta. 46, 3245-3258 (2001).
42. Fry, A. J. & Krieger, R. L. Electrolyte effects upon the polarographic reduction of alkyl halides in dimethyl sulfoxide. J. Org. Chem. 41, 54-57 (1976).
43. Pause, L., Robert, M. & Saveánt, J-M. Can single-electron transfer break an aromatic carbon-heteroatom bond in one step? A novel example of transition between stepwise and concerted mechanisms in the reduction of aromatic iodides. J. Am. Chem. Soc. 121, 7158-7159 (1999).
44. McNally, A., Prier, C. K. & MacMillan D. W. C. Discovery of an a-amino C-H arylation reaction using the strategy of accelerated serendipity. Science 334, 1114-1117 (2011).
45. King, K. A., Spellane, P. J. & Watts, R. J. Excited-state properties of a triply orthometalated iridium(III) complex. J. Am. Chem. Soc. 107, 1431-1432 (1985).
46. Narayanam, J. M. R., Tucker, J. W. & Stephenson, C. R. J. Electron-transfer photoredox catalysis: development of a tin-free reductive dehalogenation reaction. J. Am. Chem. Soc. 131, 8756-8757 (2009).
47. Tucker, J. W., Zhang, Y., Jamison, T. F. & Stephenson, C. R. J. Visible-light photoredox catalysis in flow. Angew. Chem. Int. Ed. 51, 4144-4147 (2012).
48. Baguley, P. A. & Walton, J. C. Flight from the tyranny of tin: the quest for practical radical sources free from metal encumbrances. Angew. Chem. Int. Ed. 37, 3072-3082 (1998).