Synthesis of 1,1,1-Tris(boronates) from Vinylarenes by Co-Catalyzed Dehydrogenative Borylations-Hydroboration

Journal of the American Chemical Society

Volumn 137, Issue 50, 2015, Pages 15600-15603

  Zhang, Lei ^a   Huang, Zheng ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHESIS (CHEMICAL);

BORONATE; BORONATES; HIGH YIELD; HYDROBORATION; MECHANISTIC STUDIES; PINACOLBORANE; VINYLARENES;

CATALYSIS;

1,1,1 TRIS(BORONATES); BORONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL MODIFICATION; DEHYDROGENATIVE BORYLATION; ENVIRONMENTAL TEMPERATURE; HYDROBORATION; SYNTHESIS;

EID: 84952802274     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b11366     Document Type: Article

References (55)

1. Sun, H.-Y.; Kubota, K.; Hall, D. G. Chem.-Eur. J. 2015, DOI: 10.1002/chem.201406680.
2. Joannou, M. V.; Moyer, B. S.; Meek, S. J. J. Am. Chem. Soc. 2015, 137, 6176 10.1021/jacs.5b03477
3. Coombs, J. R.; Zhang, L.; Morken, J. P. Org. Lett. 2015, 17, 1708 10.1021/acs.orglett.5b00480
4. Mlynarski, S. N.; Schuster, C. H.; Morken, J. P. Nature 2013, 505, 386 10.1038/nature12781
5. Sun, C.; Potter, B.; Morken, J. P. J. Am. Chem. Soc. 2014, 136, 6534 10.1021/ja500029w
6. Hong, K.; Liu, X.; Morken, J. P. J. Am. Chem. Soc. 2014, 136, 10581 10.1021/ja505455z
7. Li, H.; Zhang, Z.; Shangguan, X.; Huang, S.; Chen, J.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2014, 53, 11921 10.1002/anie.201407000
8. Kliman, L. T.; Mlynarski, S. N.; Ferris, G. E.; Morken, J. P. Angew. Chem., Int. Ed. 2012, 51, 521 10.1002/anie.201105716
9. Endo, K.; Ohkubo, T.; Hirokami, M.; Shibata, T. J. Am. Chem. Soc. 2010, 132, 11033 10.1021/ja105176v
10. Endo, K.; Hirokami, M.; Shibata, T. J. Org. Chem. 2010, 75, 3469 10.1021/jo1003407
11. Sieber, J. D.; Morken, J. P. J. Am. Chem. Soc. 2006, 128, 74 10.1021/ja057020r
12. Shimizu, M.; Nakamaki, C.; Shimono, K.; Schelper, M.; Kurahashi, T.; Hiyama, T. J. Am. Chem. Soc. 2005, 127, 12506 10.1021/ja054484g
13. Scheuermann, M. L.; Johnson, E. J.; Chirik, P. J. Org. Lett. 2015, 17, 2716 10.1021/acs.orglett.5b01135
14. Zhang, Z.-Q.; Yang, C.-T.; Liang, L.-J.; Xiao, B.; Lu, X.; Liu, J.-H.; Sun, Y.-Y.; Marder, T. B.; Fu, Y. Org. Lett. 2014, 16, 6342 10.1021/ol503111h
15. Cho, S. H.; Hartwig, J. F. Chem. Sci. 2014, 5, 694 10.1039/C3SC52824C
16. Li, H.; Shangguan, X.; Zhang, Z.; Huang, S.; Zhang, Y.; Wang, J. Org. Lett. 2014, 16, 448 10.1021/ol403338s
17. Feng, X.; Jeon, H.; Yun, J. Angew. Chem., Int. Ed. 2013, 52, 3989 10.1002/anie.201208610
18. Takaya, J.; Iwasawa, N. ACS Catal. 2012, 2, 1993 10.1021/cs300320u
19. Ito, H.; Kubota, K. Org. Lett. 2012, 14, 890 10.1021/ol203413w
20. Lee, J. C. H.; McDonald, R.; Hall, D. G. Nat. Chem. 2011, 3, 894 10.1038/nchem.1150
21. Endo, K.; Hirokami, M.; Shibata, T. Synlett 2009, 2009, 1331 10.1055/s-0028-1088131
22. McIsaac, D. I.; Geier, S. J.; Vogels, C. M.; Decken, A.; Westcott, S. A. Inorg. Chim. Acta 2006, 359, 2771 10.1016/j.ica.2005.10.043
23. Shimada, S.; Batsanov, A. S.; Howard, J. A. K.; Marder, T. B. Angew. Chem., Int. Ed. 2001, 40, 2168 10.1002/1521-3773(20010601)40:11<2168::AID-ANIE2168>3.3.CO;2-S
24. Castle, R. B.; Matteson, D. S. J. Organomet. Chem. 1969, 20, 19 10.1016/S0022-328X(00)80082-0
25. Matteson, D. S. Synthesis 1975, 1975, 147 10.1055/s-1975-23686
26. Mita, T.; Ikeda, Y.; Michigami, K.; Sato, Y. Chem. Commun. 2013, 49, 5601 10.1039/c3cc42675k
27. Bluhm, M.; Maderna, A.; Pritzkow, H.; Bethke, S.; Gleiter, R.; Siebert, W. Eur. J. Inorg. Chem. 1999, 1693 10.1002/(SICI)1099-0682(199910)1999:10<1693::AID-EJIC1693>3.0.CO;2-9
28. Gu, Y.; Pritzkow, H.; Siebert, W. Eur. J. Inorg. Chem. 2001, 373 10.1002/1099-0682(200102)2001:2<373::AID-EJIC373>3.0.CO;2-6
29. Baker, R. T.; Nguyen, P.; Marder, T. B.; Westcott, S. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1336 10.1002/anie.199513361
30. Nguyen, P.; Coapes, R. B.; Woodward, A. D.; Taylor, N. J.; Burke, J. M.; Howard, J. A. K.; Marder, T. B. J. Organomet. Chem. 2002, 652, 77 10.1016/S0022-328X(02)01310-4
31. Marder, T. B.; Norman, N. C. Top. Catal. 1998, 5, 63 10.1023/A:1019145818515
32. Chirik, P. J. Catalysis Without Precious Metals; Bullock, R. M., Ed.; Wiley-VCH: Weinheim, 2010; pp 83-110.
33. Junge, K.; Schroder, M.; Beller, M. Chem. Commun. 2011, 47, 4849 10.1039/c0cc05733a
34. Nakazawa, H.; Itazaki, M. Top. Organomet. Chem. 2011, 33, 27 10.1007/978-3-642-14670-1
35. Morris, R. H. Chem. Soc. Rev. 2009, 38, 2282 10.1039/b806837m
36. Sherry, B. D.; Fürstner, A. Acc. Chem. Res. 2008, 41, 1500 10.1021/ar800039x
37. Zhang, L.; Peng, D.; Leng, X.; Huang, Z. Angew. Chem., Int. Ed. 2013, 52, 3676 10.1002/anie.201210347
38. Zhang, L.; Zuo, Z.; Wan, X.; Huang, Z. J. Am. Chem. Soc. 2014, 136, 15501 10.1021/ja5093908
39. Zhang, L.; Zuo, Z.; Leng, X.; Huang, Z. Angew. Chem., Int. Ed. 2014, 53, 2696 10.1002/anie.201310096
40. Obligacion, J. V.; Chirik, P. J. J. Am. Chem. Soc. 2013, 135, 19107 10.1021/ja4108148
41. Obligacion, J. V.; Chirik, P. J. Org. Lett. 2013, 15, 2680 10.1021/ol400990u
42. Greenhalgh, M. D.; Thomas, S. P. Chem. Commun. 2013, 49, 11230 10.1039/c3cc46727a
43. Palmer, W. N.; Diao, T.; Pappas, I.; Chirik, P. J. ACS Catal. 2015, 5, 622 10.1021/cs501639r
44. Tseng, K.-N. T.; Kampf, J. W.; Szymczak, N. K. ACS Catal. 2015, 5, 411 10.1021/cs501820w
45. Chen, J.; Xi, T.; Lu, Z. Org. Lett. 2014, 16, 6452 10.1021/ol503282r
46. Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890 10.1021/cr900206p
47. Mkhalid, I. A. I.; Coapes, R. B.; Edes, S. N.; Coventry, D. N.; Souza, F. E. S.; Thomas, R. L l.; Hall, J. J.; Bi, S.-W.; Lin, Z.; Marder, T. B. Dalton Trans. 2008, 1055 10.1039/B715584K
48. Coapes, R. B.; Souza, F. E. S.; Thomas, L. R.; Hall, J. J.; Marder, T. B. Chem. Commun. 2003, 614 10.1039/b211789d
49. Bowman, A. C.; Milsmann, C.; Bill, E.; Lobkovsky, E.; Weyhermüller, T.; Wieghardt, K.; Chirik, P. J. Inorg. Chem. 2010, 49, 6110 10.1021/ic100717w
50. Schaefer, B. A.; Margulieux, G. W.; Small, B. L.; Chirik, P. J. Organometallics 2015, 34, 1307 10.1021/acs.organomet.5b00044
51. Semproni, S. P.; Atienza, C. C. H.; Chirik, P. J. Chem. Sci. 2014, 5, 1956 10.1039/c4sc00255e
52. Adams, C. J.; Baber, R. A.; Batsanov, A. S.; Bramham, G.; Charmant, J. P. H.; Haddow, M. F.; Howard, J. A. K.; Lam, W. H.; Lin, Z.; Marder, T. B.; Norman, N. C.; Orpen, A. G. Dalton Trans. 2006, 1370 10.1039/b516594f
53. Frank, R.; Howell, J.; Campos, J.; Tirfoin, R.; Phillips, Ni.; Zahn, S.; Mingos, D. M.; Aldridge, S. Angew. Chem., Int. Ed. 2015, 54, 9586 10.1002/anie.201504929
54. Takaya, J.; Kirai, N.; Iwasawa, N. J. Am. Chem. Soc. 2011, 133, 12980 10.1021/ja205186k
55. Obligacion, J. V.; Semproni, S. P.; Chirik, P. J. J. Am. Chem. Soc. 2014, 136, 4133 10.1021/ja500712z