Palladium-catalyzed ligand-promoted site-selective cyanomethylation of unactivated C(sp3)-H bonds with acetonitrile

Chemical Science

Volumn 7, Issue 4, 2016, Pages 2804-2808

  Liu, Yongbing ^a   Yang, Ke ^a,b   Ge, Haibo ^a  

^a INDIANA UNIVERSITY   (United States)

^b NANJING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; CATALYSIS; PALLADIUM;

ALIPHATIC AMIDES; BROAD APPLICATION; CHEMICAL RESEARCH; CROSS-COUPLINGS; DIRECTING GROUPS; PALLADIUM CATALYSIS; PALLADIUM-CATALYZED; SYNTHETIC ORGANIC CHEMISTRY;

C (PROGRAMMING LANGUAGE);

EID: 84961916415     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c5sc04066c     Document Type: Article

References (62)

1. F. F. Fleming Nat. Prod. Rep. 1999 16 597 606
2. F. F. Fleming L. Yao P. C. Ravikumar L. Funk B. C. Shook J. Med. Chem. 2010 53 7902 7917
3. R. López C. Palomo Angew. Chem., Int. Ed. 2015 54 13170 13184
4. Z. Rappoport, The Chemistry of the Cyano Group, Wiley-Interscience, London, 1970
5. S. P. Khanapure E. R. Biehl J. Org. Chem. 1990 55 1471 1475
6. N. Kumagai S. Matsunaga M. Shibasaki J. Am. Chem. Soc. 2004 126 13632 13633
7. B. Anxionnat D. G. Pardo G. Ricci J. Cossy Org. Lett. 2011 13 4084 4087
8. J. Velcicky A. Soicke R. Steiner H. Schmalz J. Am. Chem. Soc. 2011 133 6948 6951
9. T. Wu X. Mu G. Liu Angew. Chem., Int. Ed. 2011 50 12578 12581
10. G.-W. Wang A.-X. Zhou J.-J. Wang R.-B. Hu S.-D. Yang Org. Lett. 2013 15 5270 5273
11. S. Chakraborty Y. J. Patel J. A. Krause H. Guan Angew. Chem., Int. Ed. 2013 52 7523 7526
12. J. Shen D. Yang Y. Liu S. Qin J. Zhang J. Sun C. Liu C. Liu X. Zhao C. Chu R. Liu Org. Lett. 2014 16 350 353
13. A. Bunescu Q. Wang J. Zhu Chem.-Eur. J. 2014 20 14633 14636
14. P. J. Lindsay-Scott A. Clarke J. Richardson Org. Lett. 2015 17 476 479
15. A. D. Mamuye L. Castoldi U. Azzena W. Holzera V. Pace Org. Biomol. Chem. 2015 13 1969 1973
16. D. A. Culkin J. F. Hartwig Acc. Chem. Res. 2003 36 234 245
17. T. Frejd T. Klingstedt Synthesis 1987 40 42
18. A. Nortcliffe N. P. Botting D. O'Hagan Org. Biomol. Chem. 2013 11 4657 4671
19. O. M. Ali A. E.-G. E. Amr E. E. Mostafa Res. Chem. Intermed. 2014 40 1545 1556
20. F. Diaba C. L. Houerou M. Grignon-Dubois P. Gerval J. Org. Chem. 2000 65 907 910
21. L. Wu J. F. Hartwig J. Am. Chem. Soc. 2005 127 15824 15832
22. T. Mukaiyama M. Michida Chem. Lett. 2007 36 1244 1245
23. C. Verrier S. Oudeyer I. Dez V. Levacher Tetrahedron Lett. 2012 53 1958 1960
24. Y.-C. Fan G.-F. Du W.-F. Sun W. Kang L. He Tetrahedron Lett. 2012 53 2231 2233
25. R. Shang D.-S. Ji L. Chu Y. Fu L. Liu Angew. Chem., Int. Ed. 2011 50 4470 4474
26. P. Y. Yeung K. H. Chung F. Y. Kwong Org. Lett. 2011 13 2912 2915
27. M. Kosugi M. Ishiguro Y. Negishi H. Sano T. Migita Chem. Lett. 1984 1511 1512
28. D. A. Culkin J. F. Hartwig J. Am. Chem. Soc. 2002 124 9330 9331
29. J. You J. G. Verkade Angew. Chem., Int. Ed. 2003 42 5051 5053
30. J. You J. G. Verkade J. Org. Chem. 2003 68 8003 8007
31. H. Yoshida Y. Fujimura H. Yuzawa J. Kumagai T. Yoshida Chem. Commun. 2013 49 3793 3795
32. X. Chen K. M. Engle D.-H. Wang J.-Q. Yu Angew. Chem., Int. Ed. 2009 48 5094 5115
33. T. W. Lyons M. S. Sanford Chem. Rev. 2010 110 1147 1169
34. H. Li B.-J. Lia Z.-J. Shi Catal. Sci. Technol. 2011 1 191 206
35. G. Rouquet N. Chatani Angew. Chem., Int. Ed. 2013 52 11726 11743
36. O. Daugulis J. Roane L. D. Tran Acc. Chem. Res. 2015 48 1053 1064
37. Z. Chen B. Wang J. Zhang W. Yu Z. Liu Y. Zhang Org. Chem. Front. 2015 2 1107 1295
38. X. Chen C. E. Goodhue J.-Q. Yu J. Am. Chem. Soc. 2006 128 12634 12635
39. D.-H. Wang M. Wasa R. Giri J.-Q. Yu J. Am. Chem. Soc. 2008 130 7190 7191
40. B.-F. Shi N. Maugel Y.-H. Zhang J.-Q. Yu Angew. Chem., Int. Ed. 2008 47 4882 4886
41. L. D. Tran O. Daugulis Angew. Chem., Int. Ed. 2012 51 5188 5191
42. S.-Y. Zhang G. He W. A. Nack Y.-S. Zhao Q. Li G. Chen J. Am. Chem. Soc. 2013 135 2124 2127
43. S.-Y. Zhang Q. Li G. He W. A. Nack G. Chen J. Am. Chem. Soc. 2013 135 12135 12141
44. K. Chen F. Hu S.-Q. Zhang B.-F. Shi Chem. Sci. 2013 4 3906 3911
45. E. T. Nadres G. I. F. Santos D. Shabashov O. Daugulis J. Org. Chem. 2013 78 9689 9714
46. K. Chen B.-F. Shi Angew. Chem., Int. Ed. 2014 53 11950 11954
47. R.-Y. Zhu J. He X.-C. Wang J.-Q. Yu J. Am. Chem. Soc. 2014 136 13194 13197
48. B. Wang X. Wu R. Jiao S.-Y. Zhang W. A. Nack G. He G. Chen Org. Chem. Front. 2015 2 1318 1321
49. M. R. Netherton C. Dai K. Neuschütz G. C. Fu J. Am. Chem. Soc. 2001 123 10099 10100
50. J. H. Kirchhoff C. Dai G. C. Fu Angew. Chem., Int. Ed. 2002 41 1945 1947
51. J. H. Kirchhoff M. R. Netherton I. D. Hills G. C. Fu J. Am. Chem. Soc. 2002 124 13662 13663
52. J. Zhou G. C. Fu J. Am. Chem. Soc. 2003 125 12527 12530
53. Y. Suto N. Kumagai S. Matsunaga M. Kanai M. Shibasaki Org. Lett. 2003 5 3147 3150
54. A. Bunescu Q. Wang J. Zhu Angew. Chem., Int. Ed. 2015 54 3132 3135
55. C. Chatalova-Sazepin Q. Wang G. M. Sammis J. Zhu Angew. Chem., Int. Ed. 2015 54 5443 5446
56. Y. Suto R. Tsuji M. Kanai M. Shibasaki Org. Lett. 2005 7 3757 3760
57. P. Espinet A. M. Echavarren Angew. Chem., Int. Ed. 2004 43 4704 4734
58. C. Cordovilla C. Bartolomé J. M. Martínez-Ilarduya P. Espinet ACS Catal. 2015 5 3040 3053
59. V. Farina S. Kapadia B. Krishnan C. Wang L. S. Liebeskind J. Org. Chem. 1994 59 5905 5911
60. M. Eckhardt G. C. Fu J. Am. Chem. Soc. 2003 125 13642 13643
61. S. P. H. Mee V. Lee J. E. Baldwin Angew. Chem., Int. Ed. 2004 43 1132 1136
62. Y. Chen J. P. Romaire T. R. Newhouse J. Am. Chem. Soc. 2015 137 5875 5878