Nickel-catalyzed cross-couplings of benzylic pivalates with arylboroxines: Stereospecific formation of diarylalkanes and triarylmethanes

Journal of the American Chemical Society

Volumn 135, Issue 9, 2013, Pages 3307-3310

  Zhou, Qi ^a   Srinivas, Harathi D ^a   Dasgupta, Srimoyee ^a   Watson, Mary P ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLIC; CROSS-COUPLINGS; DIARYLALKANES; STEREOSPECIFIC;

CATALYSIS;

NICKEL;

ALKANE DERIVATIVE; BENZYL ALCOHOL DERIVATIVE; BENZYLIC PIVALATE DERIVATIVE; METHANE; NICKEL; ORGANOBORON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; STEREOSPECIFICITY; SYNTHESIS;

ALKANES; BENZYL COMPOUNDS; BORON COMPOUNDS; CATALYSIS; METHANE; MOLECULAR STRUCTURE; NICKEL; ORGANOMETALLIC COMPOUNDS; PENTANOIC ACIDS; STEREOISOMERISM;

EID: 84874917475     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja312087x     Document Type: Article

References (44)

1. Zhang, J.; Bellomo, A.; Creamer, A. D.; Dreher, S. D.; Walsh, P. J. J. Am. Chem. Soc. 2012, 134, 13765
2. Cheltsov, A. V.; Aoyagi, M.; Aleshin, A.; Yu, E. C.-W.; Gilliland, T.; Zhai, D.; Bobkov, A. A.; Reed, J. C.; Liddington, R. C.; Abagyan, R. J. Med. Chem. 2010, 53, 3899
3. Huang, Z.; Ducharme, Y.; Macdonald, D.; Robichaud, A. Curr. Opin. Chem. Biol. 2001, 5, 432
4. Alami, M.; Messauoudi, S.; Hamze, A.; Provot, O.; Brion, J.-D.; Liu, J.-M.; Bignon, J.; Bakala, J. Dihydro-Iso-Ca-4 and Analogues: Potent Cytotoxics, Inhibitors of Tubulin Polymerization. WO2009/147217, 2009.
5. Messaoudi, S.; Hamze, A.; Provot, O.; Tréguier, B.; Rodrigo De Losada, J.; Bignon, J.; Liu, J.-M.; Wdzieczak-Bakala, J.; Thoret, S.; Dubois, J.; Brion, J.-D.; Alami, M. ChemMedChem 2011, 6, 488
6. Moree, W. J.; Li, B.-F.; Jovic, F.; Coon, T.; Yu, J.; Gross, R. S.; Tucci, F.; Marinkovic, D.; Zamani-Kord, S.; Malany, S.; Bradbury, M. J.; Hernandez, L. M.; O'Brien, Z.; Wen, J.; Wang, H.; Hoare, S. R. J.; Petroski, R. E.; Sacaan, A.; Madan, A.; Crowe, P. D.; Beaton, G. J. Med. Chem. 2009, 52, 5307
7. Beaton, G.; Moree, W. J.; Jovic, F.; Coon, T.; Yu, J. Sleep Inducing Compound and Methods Relating Thereto. US2006/14797, 2006.
8. Luan, Y.; Schaus, S. E. J. Am. Chem. Soc. 2012, 134, 19965
9. Fessard, T. C.; Andrews, S. P.; Motoyoshi, H.; Carreira, E. M. Angew. Chem., Int. Ed. 2007, 46, 9331
10. Lewis, C. A.; Chiu, A.; Kubryk, M.; Balsells, J.; Pollard, D.; Esser, C. K.; Murry, J.; Reamer, R. A.; Hansen, K. B.; Miller, S. J. J. Am. Chem. Soc. 2006, 128, 16454
11. Pathak, T. P.; Gligorich, K. M.; Welm, B. E.; Sigman, M. S. J. Am. Chem. Soc. 2010, 132, 7870
12. Nave, S.; Sonawane, R. P.; Elford, T. G.; Aggarwal, V. K. J. Am. Chem. Soc. 2010, 132, 17096
13. Roesner, S.; Casatejada, J. M.; Elford, T. G.; Sonawane, R. P.; Aggarwal, V. K. Org. Lett. 2011, 13, 5740
14. Bolshan, Y.; Chen, C.-y.; Chilenski, J. R.; Gosselin, F.; Mathre, D. J.; O'Shea, P. D.; Roy, A.; Tillyer, R. D. Org. Lett. 2004, 6, 111
15. Arp, F. O.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 10482
16. Binder, J. T.; Cordier, C. J.; Fu, G. C. J. Am. Chem. Soc. 2012, 134, 17003
17. López-Pérez, A.; Adrio, J.; Carretero, J. C. Org. Lett. 2009, 11, 5514
18. Molander, G. A.; Elia, M. D. J. Org. Chem. 2006, 71, 9198
19. Kuwano, R. J. Synth. Org. Chem., Jpn. 2011, 69, 1263
20. Kofink, C. C.; Knochel, P. Org. Lett. 2006, 8, 4121
21. McLaughlin, M. Org. Lett. 2005, 7, 4875
22. Guan, B.-T.; Xiang, S.-K.; Wang, B.-Q.; Sun, Z.-P.; Wang, Y.; Zhao, K.-Q.; Shi, Z.-J. J. Am. Chem. Soc. 2008, 130, 3268
23. Yu, D.-G.; Wang, X.; Zhu, R.-Y.; Luo, S.; Zhang, X.-B.; Wang, B.-Q.; Wang, L.; Shi, Z.-J. J. Am. Chem. Soc. 2012, 134, 14639
24. Greene, M. A.; Yonova, I. M.; Williams, F. J.; Jarvo, E. R. Org. Lett. 2012, 14, 4293
25. Taylor, B. L. H.; Harris, M. R.; Jarvo, E. R. Angew. Chem., Int. Ed. 2012, 51, 7790
26. Taylor, B. L. H.; Swift, E. C.; Waetzig, J. D.; Jarvo, E. R. J. Am. Chem. Soc. 2011, 133, 389
27. He, A.; Falck, J. R. J. Am. Chem. Soc. 2010, 132, 2524
28. For our recently developed stereospecific cross-coupling of benzylic ammonium triflates with boronic acids, see: Maity, P.; Shacklady-McAtee, D. M.; Yap, G. P. A.; Sirianni, E. R.; Watson, M. P. J. Am. Chem. Soc. 2013, 135, 280
29. Tian has reported the copper-catalyzed coupling of benzylic sulfonimides with Grignard reagents. See: Li, M.-B.; Tang, X.-L.; Tian, S.-K. Adv. Synth. Catal. 2011, 353, 1980
30. Imao, D.; Glasspoole, B. W.; Laberge, V. S.; Crudden, C. M. J. Am. Chem. Soc. 2009, 131, 5024
31. Ohmura, T.; Awano, T.; Suginome, M. J. Am. Chem. Soc. 2010, 132, 13191
32. Awano, T.; Ohmura, T.; Suginome, M. J. Am. Chem. Soc. 2011, 133, 20738
33. Sandrock, D. L.; Jean-Gérard, L.; Chen, C.-y.; Dreher, S. D.; Molander, G. A. J. Am. Chem. Soc. 2010, 132, 17108
34. Lee, J. C. H.; McDonald, R.; Hall, D. G. Nat. Chem. 2011, 3, 894
35. Kuwano, R.; Yokogi, M. Chem. Commun. 2005, 5899
36. Yu, J.-Y. J.; Kuwano, R. Org. Lett. 2008, 10, 973
37. Huang, K.; Li, G.; Huang, W.-P.; Yu, D.-G.; Shi, Z.-J. Chem. Commun. 2011, 47, 7224
38. Ehle, A. R.; Zhou, Q.; Watson, M. P. Org. Lett. 2012, 14, 1202
39. Quasdorf, K. W.; Tian, X.; Garg, N. K. J. Am. Chem. Soc. 2008, 130, 14422
40. Li, B.-J.; Xu, L.; Wu, Z.-H.; Guan, B.-T.; Sun, C.-L.; Wang, B.-Q.; Shi, Z.-J. J. Am. Chem. Soc. 2009, 131, 14656
41. Guan, B.-T.; Wang, Y.; Li, B.-J.; Yu, D.-G.; Shi, Z.-J. J. Am. Chem. Soc. 2008, 130, 14468
42. Xiao, Q.; Tian, L.; Tan, R.; Xia, Y.; Qiu, D.; Zhang, Y.; Wang, J. Org. Lett. 2012, 14, 4230
43. Similar β-hydride elimination experiments were used to probe the oxidative addition step of Suzuki cross-couplings of alkyl tosylates. See: Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 3910
44. Retention of configuration in reductive elimination is well-precedented. See: Stille, J. K. Oxidative Addition and Reductive Elimination. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R.; Patai, S., Eds.; Wiley: New York, 1985; Vol. 2, pp 625 ff.