Manganese-Catalyzed Borylation of Unactivated Alkyl Chlorides

Journal of the American Chemical Society

Volumn 138, Issue 19, 2016, Pages 6139-6142

  Atack, Thomas C ^a   Cook, Silas P ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; MANGANESE;

ALKYL CHLORIDES; CATALYST LOADINGS; CATALYZED COUPLING; CONTROLLED REACTIONS; CROSS-COUPLINGS; DIRECT BORYLATION; RADICAL PROCESS; TETRAMETHYLETHYLENEDIAMINE;

CHLORINE COMPOUNDS;

ALKYL HALIDE; BIS PINACOLATO DIBORON; BORON DERIVATIVE; BORONIC ACID DERIVATIVE; CHLORIDE; ESTER DERIVATIVE; ETHYLENEDIAMINE DERIVATIVE; HALIDE; MANGANESE; MANGANESE BROMIDE; MANGANESE DERIVATIVE; RADICAL; TETRAMETHYLETHYLENEDIAMINE; UNCLASSIFIED DRUG;

ARTICLE; BORYLATION; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; REACTION OPTIMIZATION; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 84971280092     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.6b03157     Document Type: Article

References (32)

1. Cahiez, G.; Duplais, C.; Buendia, J. Chem. Rev. 2009, 109, 1434 10.1021/cr800341a
2. McGarrigle, E. M.; Gilheany, D. G. Chem. Rev. 2005, 105, 1563 10.1021/cr0306945
3. Wu, A. J.; Penner-Hahn, J. E.; Pecoraro, V. L. Chem. Rev. 2004, 104, 903 10.1021/cr020627v
4. Zhou, B.; Chen, H.; Wang, C. J. Am. Chem. Soc. 2013, 135, 1264 10.1021/ja311689k
5. He, R.; Huang, Z. T.; Zheng, Q. Y.; Wang, C. Angew. Chem., Int. Ed. 2014, 53, 4950 10.1002/anie.201402575
6. Casas, A.; Merlos, M.; Castaner, J. Drugs Future 1997, 22, 481 10.1358/dof.1997.022.05.407271
7. Kang, S. K.; Kim, J. S.; Choi, S. C. J. Org. Chem. 1997, 62, 4208 10.1021/jo970656j
8. Cahiez, G.; Lepifre, F.; Ramiandrasoa, P. Synthesis 1999, 1999, 2138 10.1055/s-1999-3644
9. Cahiez, G.; Luart, D.; Lecomte, F. Org. Lett. 2004, 6, 4395 10.1021/ol048842g
10. Cahiez, G.; Gager, O.; Lecomte, F. Org. Lett. 2008, 10, 5255 10.1021/ol802273e
11. Alami, M.; Ramiandrasoa, P.; Cahiez, G. Synlett 2000, 9, 325 10.1055/s-0033-1338580
12. Liu, T. J.; Yi, C. L.; Chan, C. C.; Lee, C. F. Chem.-Asian J. 2013, 8, 1029 10.1002/asia.201300045
13. Li, L.; Zhao, S.; Joshi-Pangu, A.; Diane, M.; Biscoe, M. R. J. Am. Chem. Soc. 2014, 136, 14027 10.1021/ja508815w
14. Dreher, S. D.; Dormer, P. G.; Sandrock, D. L.; Molander, G. A. J. Am. Chem. Soc. 2008, 130, 9257 10.1021/ja8031423
15. van den Hoogenband, A.; Lange, J. H. M.; Terpstra, J. W.; Koch, M.; Visser, G. M.; Visser, M.; Korstanje, T. J.; Jastrzebski, J. T. B. H. Tetrahedron Lett. 2008, 49, 4122 10.1016/j.tetlet.2008.04.129
16. Joshi-Pangu, A.; Ma, X.; Diane, M.; Iqbal, S.; Kribs, R. J.; Huang, R.; Wang, C. Y.; Biscoe, M. R. J. Org. Chem. 2012, 77, 6629 10.1021/jo301156e
17. Yi, J.; Liu, J.-H.; Liang, J.; Dai, J.-J.; Yang, C.-T.; Fu, Y.; Liu, L. Adv. Synth. Catal. 2012, 354, 1685 10.1002/adsc.201200136
18. Bej, A.; Srimani, D.; Sarkar, A. Green Chem. 2012, 14, 661 10.1039/c2gc16111g
19. Dudnik, A. S.; Fu, G. C. J. Am. Chem. Soc. 2012, 134, 10693 10.1021/ja304068t
20. Ito, H.; Kubota, K. Org. Lett. 2012, 14, 890 10.1021/ol203413w
21. Yang, C. T.; Zhang, Z. Q.; Tajuddin, H.; Wu, C. C.; Liang, J.; Liu, J. H.; Fu, Y.; Czyzewska, M.; Steel, P. G.; Marder, T. B.; Liu, L. Angew. Chem., Int. Ed. 2012, 51, 528 10.1002/anie.201106299
22. Bose, S. K.; Fucke, K.; Liu, L.; Steel, P. G.; Marder, T. B. Angew. Chem., Int. Ed. 2014, 53, 1799 10.1002/anie.201308855
23. Atack, T. C.; Lecker, R. M.; Cook, S. P. J. Am. Chem. Soc. 2014, 136, 9521 10.1021/ja505199u
24. Bedford, R. B.; Brenner, P. B.; Carter, E.; Gallagher, T.; Murphy, D. M.; Pye, D. R. Organometallics 2014, 33, 5940 10.1021/om500847j
25. Hong, K.; Liu, X.; Morken, J. P. J. Am. Chem. Soc. 2014, 136, 10581 10.1021/ja505455z
26. 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
27. Lipani, Z.; Catalano, M. R.; Rossi, P.; Paoli, P.; Malandrino, G. Chem. Vap. Deposition 2013, 19, 22 10.1002/cvde.201207017
28. Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317 10.1021/ar50153a004
29. Lal, D.; Griller, D.; Husband, S.; Ingold, K. U. J. Am. Chem. Soc. 1974, 96, 6355 10.1021/ja00827a018
30. Kochi, J. K. Acc. Chem. Res. 1974, 7, 351 10.1021/ar50082a006
31. Lu, Z.; Fu, G. C. Angew. Chem., Int. Ed. 2010, 49, 6676 10.1002/anie.201003272
32. Grotewold, J.; Lissi, E. A.; Scaiano, J. C. J. Organomet. Chem. 1969, 19, 431 10.1016/S0022-328X(00)85317-6