Photoredox Generation of Carbon-Centered Radicals Enables the Construction of 1,1-Difluoroalkene Carbonyl Mimics

Angewandte Chemie - International Edition

Volumn 56, Issue 47, 2017, Pages 15073-15077

  Lang, Simon B ^a   Wiles, Rebecca J ^a   Kelly, Christopher B ^a   Molander, Gary A ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

alkenes; alkylation; fluorine; photochemistry; radicals

Indexed keywords

ALKYLATION; FLUORINE; OLEFINS; PHOTOCHEMICAL REACTIONS;

CARBON RADICALS; CARBON-CENTERED RADICALS; RADICALS; SUBSTITUTED ALKENE; TERTIARY RADICALS; TRIFLUOROMETHYL; VISIBLE LIGHT;

HYDROCARBONS;

ALKENE; BORON DERIVATIVE; CARBON; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FLUORENE; FLUORENE DERIVATIVE;

ALKYLATION; CHEMISTRY; MOLECULAR MIMICRY; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKENES; ALKYLATION; BORON COMPOUNDS; CARBON; FLUORENES; INDICATORS AND REAGENTS; MOLECULAR MIMICRY; OXIDATION-REDUCTION; PHOTOCHEMICAL PROCESSES; STEREOISOMERISM;

EID: 85033785267     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201709487     Document Type: Article

References (57)

1. D. F. Veber, S. R. Johnson, H.-Y. Cheng, B. R. Smith, K. W. Wards, K. D. Kopple, J. Med. Chem. 2002, 45, 2615;
2. P. D. Leeson, B. Springthorpe, Nat. Rev. Drug Discovery 2007, 6, 881;
3. B. Agoram, W. S. Woltosz, M. B. Bolger, Adv. Drug Delivery Rev. 2001, 50, S41;
4. B. J. Aungst, J. Pharm. Sci. 2017, 106, 921.
5. C. A. Veale, J. R. Damewood, Jr., G. B. Steelman, C. Bryant, B. Gomes, J. Williams, J. Med. Chem. 1996, 38, 86;
6. A. S. Madsen, C. A. Olsen, Med. Chem. Commun. 2016, 7, 464;
7. E. R. Ottosen, M. D. Sørensen, F. Björkling, T. Skak-Nielsen, M. S. Fjording, H. Aaes, L. Binderup, J. Med. Chem. 2003, 46, 5651;
8. D. M. Goldstein, T. Alfredson, J. Bertrand, M. F. Browner, K. Clifford, S. A. Dalrymple, J. Dunn, J. Freire-Moar, S. Harris, S. S. Labadie, J. La Fargue, J. M. Lapierre, S. Larrabee, F. Li, E. Papp, D. McWeeney, C. Ramesha, R. Roberts, D. Rotstein, B. S. Pablo, E. B. Sjogren, O.-Y. So, F. X. Talamas, W. Tao, A. Trejo, A. Villasenor, M. Welch, T. Welch, P. Weller, P. E. Whiteley, K. Young, S. Zipfel, J. Med. Chem. 2006, 49, 1562.
9. P. Malátková, V. Wsól, Drug Metab. Rev. 2014, 46, 96;
10. T. Matsunaga, S. Shintani, A. Hara, Drug Metab. Pharmacokinet. 2006, 21, 1;
11. O. A. Barski, S. M. Tipparaju, A. Bhatnagar, Drug Metab. Rev. 2008, 40, 553.
12. N. A. Meanwell, J. Med. Chem. 2011, 54, 2529.
13. K. Uneyama, Hydrogen Bonding in Organofluorine Compounds in Organofluorine Chemistry, Blackwell Publishing, Oxford, UK, 2006.
14. G. Magueur, B. Crousse, M. Ourévitch, D. Bonnet-Delpon, J.-P. Bégué, J. Fluorine Chem. 2006, 127, 637;
15. C. Leriche, X. He, C.-w. Chang, H.-w. Liu, J. Am. Chem. Soc. 2003, 125, 6348.
16. J.-M. Altenburger, G. Y. Lassalle, M. Matrougui, D. Galtier, J.-C. Jetha, Z. Bocskei, C. N. Berry, C. Lunven, J. Lorrain, J.-P. Herault, P. Schaeffer, S. E. O'Connor, J.-M. Herbert, Bioorg. Med. Chem. 2004, 12, 1713;
17. Y. Pan, J. Qiu, R. B. Silverman, J. Med. Chem. 2003, 46, 5292.
18. G. Chelucci, Chem. Rev. 2012, 112, 1344;
19. X. Zhang, S. Cao, Tetrahedron Lett. 2017, 58, 375;
20. M. Hu, C. Ni, L. Li, Y. Han, J. Hu, J. Am. Chem. Soc. 2015, 137, 14496.
21. For an overview see: J. K. Matsui, S. B. Lang, D. R. Heitz, G. A. Molander, ACS Catal. 2017, 7, 2563.
22. Although the reduction potentials of α-trifluoromethyl radicals are unknown, they certainly lie below the known potential for their corresponding alkyl congeners and thus would be within the window of the reduced ground state of many photocatalysts. See: D. D. M. Wayner, D. J. McPhee, D. Griller, J. Am. Chem. Soc. 1988, 110, 132; and
23. 3 group. See:
24. D. Ryu, D. N. Primer, J. C. Tellis, G. A. Molander, Chem. Eur. J. 2016, 22, 120.
25. This type of reactivity has been observed with organolithium species previously. See:
26. J.-P. Bégué, D. Bonnet-Delpon, M. H. Rock, Tetrahedron Lett. 1995, 36, 5003;
27. J.-P. Bégué, D. Bonnet-Delpon, M. H. Rock, J. Chem. Soc. Perkin Trans. 1 1996, 1409; For a theoretical study indicating that β-fluoride elimination proceeds preferentially by an E1cB-type mechanism, see:
28. S. Alunni, F. De Angelis, L. Ottavi, M. Papavasileiou, F. Tarantelli, J. Am. Chem. Soc. 2005, 127, 15151.
29. T. Xiao, L. Li, L. Zhou, J. Org. Chem. 2016, 81, 7908;
30. L. Li, T. Xiao, H. Chen, L. Zhou, Chem. Eur. J. 2017, 23, 2249.
31. J. Luo, J. Zhang, ACS Catal. 2016, 6, 873.
32. M. A. Brumfield, S. L. Quillen, U. C. Yoon, P. S. Mariano, J. Am. Chem. Soc. 1984, 106, 6855;
33. G. Pandey, G. Kumaraswamny, U. T. Bhalerao, Tetrahedron Lett. 1989, 30, 6059;
34. Z. Su, P. S. Mariano, D. E. Falvey, U. C. Yoon, S. W. Oh, J. Am. Chem. Soc. 1998, 120, 10676;
35. L. Ruiz Espelt, I. S. McPherson, E. M. Wiensch, T. P. Yoon, J. Am. Chem. Soc. 2015, 137, 2452;
36. S.-Y. Hsieh, J. W. Bode, Org. Lett. 2016, 18, 2098;
37. C. Remeur, C. B. Kelly, N. R. Patel, G. A. Molander, ACS Catal. 2017, 7, 6065.
38. D. Matsuoka, Y. Nishigaichi, Chem. Lett. 2014, 43, 559;
39. D. Matsuoka, Y. Nishigaichi, Chem. Lett. 2015, 44, 163;
40. V. Corcé, L.-M. Chamoreau, E. Derat, J.-P. Goddard, C. Ollivier, L. Fensterbank, Angew. Chem. Int. Ed. 2015, 54, 11414;
41. Angew. Chem. 2015, 127, 11576;
42. M. Jouffroy, D. N. Primer, G. A. Molander, J. Am. Chem. Soc. 2016, 138, 475; These species have also been used for radical addition into imines. See:
43. N. R. Patel, C. B. Kelly, A. P. Siegenfeld, G. A. Molander, ACS Catal. 2017, 7, 1766.
44. Reviews on Ni/photoredox cross-coupling:
45. J. C. Tellis, C. B. Kelly, D. N. Primer, M. Jouffroy, N. R. Patel, G. A. Molander, Acc. Chem. Res. 2016, 49, 1429;
46. Y.-Y. Gui, L. Sun, Z.-P. Lu, D.-G. Yu, Org. Chem. Front. 2016, 3, 522;
47. K. L. Skubi, T. R. Blum, T. P. Yoon, Chem. Rev. 2016, 116, 10035;
48. C. B. Kelly, N. R. Patel, D. N. Primer, M. Jouffroy, J. C. Tellis, G. A. Molander, Nat. Protoc. 2017, 12, 472;
49. M. D. Levin, S. Kim, F. D. Toste, ACS Cent. Sci. 2016, 2, 293;
50. M. H. Shaw, J. Twilton, D. W. C. MacMillan, J. Org. Chem. 2016, 81, 6898.
51. R.-q. Pan, X.-x. Liu, M.-z. Deng, J. Fluorine Chem. 1999, 95, 167.
52. Several examples of couplings of α-(trifluoromethyl)ethenyl boronic acid exist. The material is never isolated because of its inherent instability. It is always used crude directly after its synthesis and often in large excess. See:
53. B. Jiang, Q.-F. Wang, C.-G. Yang, M. Xu, Tetrahedron Lett. 2001, 42, 4038;
54. T. Ichitsuka, T. Fujita, T. Arita, J. Ichikawa, Angew. Chem. Int. Ed. 2014, 53, 7564;
55. Angew. Chem. 2014, 126, 7694.
56. 3,3,3-Trifluoroisopropenyllithium is notoriously unstable and decomposes to generate allenes even at temperatures below −90 °C. See: F. G. Drakesmith, O. J. Stewart, P. Tarrant, J. Org. Chem. 1968, 33, 280; Although the corresponding organozinc is known, its preparation is quite arduous and can only be used in cross-coupling with a very limited number of systems. Moreover, this reagent must be stored in solution under argon. See:
57. B. Jiang, Y. Xu, J. Org. Chem. 1991, 56, 7336.