Visible light promoted carbodifluoroalkylation of allylic alcohols via concomitant 1,2-aryl migration

Chemical Communications

Volumn 51, Issue 33, 2015, Pages 7222-7225

  Xu, Pan ^a   Hu, Kaidong ^a   Gu, Zhangxi ^a   Cheng, Yixiang ^a   Zhu, Chengjian ^a,b  

^a NANJING UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,5 DICARBONYL DERIVATIVE; ALLYL ALCOHOL; CARBONYL DERIVATIVE; LIGAND; METAL; RADICAL; SOLVENT; UNCLASSIFIED DRUG; BENZENE DERIVATIVE; PROPANOL;

ALKYLATION; ARTICLE; CARBODIFLUOROALKYLATION; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; LIGHT; MIGRATION; PHOTOCATALYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; CATALYSIS; CHEMISTRY; PHOTOCHEMISTRY;

ALKYLATION; BENZENE DERIVATIVES; CATALYSIS; LIGHT; PHOTOCHEMICAL PROCESSES; PROPANOLS;

EID: 84927753891     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c5cc01189b     Document Type: Article

References (61)

1. V. D. Romanenko V. P. Kukhar Chem. Rev. 2006 106 3868
2. K. Muller C. Faeh F. Diederich Science 2007 317 1881
3. I. Ojima, Fluorine in Medicinal Chemistry and Chemical Biology, Wiley-Blackwell, 2009
4. T. Liang C. N. Neumann T. Ritter Angew. Chem., Int. Ed. 2013 52 8214
5. V. V. Grushin Acc. Chem. Res. 2010 43 160
6. D. Cahard X. Xu S. Couve-Bonnaire X. Pannecoucke Chem. Soc. Rev. 2010 39 558
7. T. Furuya A. S. Kamlet T. Ritter Nature 2011 473 470
8. A. Lin B. Huehls J. Yang Org. Chem. Front. 2014 1 434 438
9. A. Studer Angew. Chem., Int. Ed. 2012 51 8950
10. J. Nie H. Guo D. Cahard J. Ma Chem. Rev. 2011 111 455
11. T. Furuya A. S. Kamlet T. Ritter Nature 2011 473 470
12. O. A. Tomashenko V. V. Grushin Chem. Rev. 2011 111 4475
13. G. K. S. Prakash S. K. Ganesh J.-P. Jones A. Kulkarni K. Masood J. K. Swabeck G. A. Olah Angew. Chem., Int. Ed. 2012 51 12090
14. Y. Fujiwara J. A. Dixon R. A. Rodriguez R. D. Baxter D. D. Dixon M. R. Collins D. G. Blackmond P. S. Baran J. Am. Chem. Soc. 2012 134 1494
15. Q. Zhou A. Ruffoni R. Gianatassio Y. Fujiwara E. Sella D. Shabat P. S. Baran Angew. Chem., Int. Ed. 2013 52 3949
16. Z. Feng Q.-Q. Min Y.-L. Xiao B. Zhang X. Zhang Angew. Chem., Int. Ed. 2014 53 1669
17. V. Reutrakul T. Thongpaisanwong P. Tuchinda C. Kuhakarn M. Pohmakotr J. Org. Chem. 2004 69 6913
18. F. Xiao F. Wu Y. Shen L. Zhou J. Fluorine Chem. 2005 126 63
19. Y. Li J. Liu L. Zhang L. Zhu J. Hu J. Org. Chem. 2007 72 5824
20. X. Yang Z. Wang Y. Zhu X. Fang X. Yang F. Wu Y. Shen J. Fluorine Chem. 2007 128 1046
21. M.-C. Belhomme T. Poisson X. Pannecoucke Org. Lett. 2013 15 3428
22. J. Xuan W.-J. Xiao Angew. Chem., Int. Ed. 2012 51 6828
23. T. P. Yoon M. A. Ischay J. Du Nat. Chem. 2010 2 527
24. J. M. R. Narayanam C. R. J. Stephenson Chem. Soc. Rev. 2011 40 102
25. J. W. Tucker C. R. J. Stephenson J. Org. Chem. 2012 77 1617
26. C. K. Prier D. A. Rankic D. W. C. MacMillan Chem. Rev. 2013 113 5322
27. Y. Xi H. Yi A. Lei Org. Biomol. Chem. 2013 11 2387
28. J. Xie H. Jin P. Xu C. Zhu Tetrahedron Lett. 2014 55 36
29. J. D. Nguyen J. W. Tucker M. D. Konieczynska C. R. J. Stephenson J. Am. Chem. Soc. 2011 133 4160
30. C. J. Wallentin J. D. Nguyen P. Finkbeiner C. R. J. Stephenson J. Am. Chem. Soc. 2012 134 8875
31. Y.-M. Su Y. Hou F. Yin Y.-M. Xu Y. Li X. Zheng X.-S. Wang Org. Lett. 2014 16 2958
32. X. Sun S. Yu Org. Lett. 2014 16 2938
33. W. Li X. Zhu H. Mao Z. Tang C. Zhu Chem. Commun. 2014 50 7521
34. L. Wang X. Wei W. Jia J. Zhong Li. Wu Q. Liu Org. Lett. 2014 16 5842
35. J. Jung E. Kim Y. You E. Cho Adv. Synth. Catal. 2014 356 2741
36. C. Yu N. Iqbal S. Park E. Cho Chem. Commun. 2014 50 12884
37. P. Xu J. Xie Q. Xue C. Pan Y. Cheng C. Zhu Chem.-Eur. J. 2013 19 14039
38. J. Xie P. Xu H. Li Q. Xue H. Jin Y. Cheng C. Zhu Chem. Commun. 2013 49 5672
39. P. Xu A. Abdukader K. Hu Y. Cheng C. Zhu Chem. Commun. 2014 50 2308
40. H. Li F.-M. Zhang Y.-Q. Tu Q.-W. Zhang Z.-M. Chen Z.-H. Chen J. Li Chem. Sci. 2011 2 1839
41. Z. Chen W. Bai S. Wang B. Yang Y.-Q. Tu F.-M. Zhang Angew. Chem., Int. Ed. 2013 52 9781
42. X. Liu F. Xiong X. Huang L. Xu P. Li X. Wu Angew. Chem., Int. Ed. 2013 52 6962
43. H. Egami R. Shimizu Y. Usui M. Sodeoka Chem. Commun. 2013 49 7346
44. M. Salamone M. Bietti Synlett 2014 1803
45. Z.-M. Chen Z. Zhang Y.-Q. Tu M.-H. Xu F.-M. Zhang C.-C. Li S.-H. Wang Chem. Commun. 2014 50 10805
46. X.-Q. Chu H. Meng Y. Zi X.-P. Xu S.-J. Ji Chem.-Eur. J. 2014 20 17198
47. Y. Li B. Liu H.-B. Li Q. Wang J.-H. Li Chem. Commun. 2015 51 1024
48. A. Bunescu Q. Wang J. Zhu Angew. Chem., Int. Ed. 2015 54 3132
49. R. Christoph H. Roland Chem. Ber. 1965 98 2471
50. A. Studer M. Bossart Tetrahedron 2001 57 9649
51. C. S. Aureliano Antunes M. Bietti G. Ercolani O. Lanzalunga M. Salamone J. Org. Chem. 2005 70 3884
52. T. J. Snape Chem. Soc. Rev. 2007 36 1823
53. B. Wang Y. Tu Acc. Chem. Res. 2011 44 1207
54. K. Umland S. Kirsch Synlett 2013 1471
55. D. A. Nagib D. W. C. MacMillan Nature 2011 480 224
56. Y. Yasu T. Koike M. Akita Angew. Chem., Int. Ed. 2012 51 9567
57. E. Kim S. Choi H. Kim E. J. Cho Chem.-Eur. J. 2013 19 6209
58. Y. Yasu T. Koike M. Akita Chem. Commun. 2013 49 2037
59. S. Mizuta S. Verhoog K. M. Engle T. Khotavivattana M. O'Duill K. Wheelhouse G. Rassias M. Médebielle V. Gouverneur J. Am. Chem. Soc. 2013 135 2505
60. N. Iqbal J. Jung S. Park E. J. Cho Angew. Chem., Int. Ed. 2014 53 539
61. J. Xie X. Yuan A. Abdukader C. Zhu J. Ma Org. Lett. 2014 16 1768