Highly efficient synthesis of alkylboronate esters via Cu(II)-Catalyzed borylation of unactivated alkyl bromides and chlorides in air

ACS Catalysis

Volumn 6, Issue 12, 2016, Pages 8332-8335

  Bose, Shubhankar Kumar ^a   Brand, Simon ^a   Omoregie, Helen Oluwatola ^b   Haehnel, Martin ^a   Maier, Jonathan ^a   Bringmann, Gerhard ^a   Marder, Todd B ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b UNIVERSITY OF IBADAN   (Nigeria)

Author keywords

Boron; C X activation; Cross coupling; N heterocyclic carbenes; Suzuki Miyaura

Indexed keywords

BORON; CATALYSIS; CHLORINE COMPOUNDS; ORGANIC COMPOUNDS;

ALKYL BROMIDES; ALKYL CHLORIDES; ALKYL HALIDES; CROSS-COUPLINGS; EFFICIENT SYNTHESIS; ELECTRON PROCESS; HIGH YIELD; N-HETEROCYCLIC CARBENES;

COPPER COMPOUNDS;

EID: 85046680870     PISSN: None     EISSN: 21555435     Source Type: Journal    
DOI: 10.1021/acscatal.6b02918     Document Type: Article

References (66)

1. (a) Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417−1492.
2. (b) Boronic AcidsPreparation and Applications in Organic Synthesis, Medicine and Materials, 2nd Edition; Hall, D. G., Ed.; Wiley−VCH: Weinheim, Germany, 2011.
3. (a) Rudolph, A.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 2656−2670.
4. (b) Imao, D.; Glasspoole, B. W.; Laberge, V. S.; Crudden, C. M. J. Am. Chem. Soc. 2009, 131, 5024−5025.
5. (c) Frisch, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674−688.
6. (a) Beenen, M. A.; An, C.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 6910−6911.
7. (b) Milo, L. J.; Lai, J. H., Jr.; Wu, W.; Liu, Y.; Maw, H.; Li, Y.; Jin, Z.; Shu, Y.; Poplawski, S. E.; Wu, Y.; Sanford, D. G.; Sudmeier, J. L.; Bachovchin, W. W. J. Med. Chem. 2011, 54, 4365− 4377.
8. (a) Zweifel, G.; Brown, H. C. In Organic Reactions, Vol. 13; John Wiley and Sons: Hoboken, NJ, 2011; pp 1−54.
9. (b) Brown, H. C. Organic Synthesis via Organoboranes; Wiley Interscience: New York, 1975.
10. (c) Brown, H. C.; Cole, T. E. Organometallics 1983, 2, 1316− 1319.
11. For olefin hydroboration, see: (a) Mannig, D.; Nöth, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 878−879.
12. (b) Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179−1191.
13. (c) Burgess, K.; van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. J. Am. Chem. Soc. 1992, 114, 9350−9359.
14. (d) Evans, D. A.; Fu, G. C.; Hoveyda, A. H. J. Am. Chem. Soc. 1992, 114, 6671−6679.
15. (e) Edwards, D. R.; Crudden, C. M.; Yam, K. Adv. Synth. Catal. 2005, 347, 50−54.
16. For alkane C−H borylation: (a) Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890−931.
17. (b) Hartwig, J. F. Acc. Chem. Res. 2012, 45, 864−873.
18. For metal-catalyzed β-borylation of α,β-unsaturated carbonyls, see: (a) Lawson, Y. G.; Lesley, M. J. G.; Norman, N. C.; Rice, C. R.; Lawson, Y. G.; Marder, T. B. Chem. Commun. 1997, 2051−2052.
19. (b) Takahashi, K.; Ishiyama, T.; Miyaura, N. Chem. Lett. 2000, 29, 982−983.
20. (c) Ito, H.; Yamanaka, H.; Tateiwa, J.; Hosomi, A. Tetrahedron Lett. 2000, 41, 6821−6825.
21. (d) Bell, N. J.; Cox, A. J.; Cameron, N. R.; Evans, J. S. O.; Marder, T. B.; Duin, M. A.; Elsevier, C. J.; Baucherel, X.; Tulloch, A. A. D.; Tooze, R. P. Chem. Commun. 2004, 1854−1855.
22. (e) Dang, L.; Lin, Z.; Marder, T. B. Organometallics 2008, 27, 4443−4454.
23. (f) Wu, H.; Radomkit, S.; O’Brien, J. M.; Hoveyda, A. H. J. Am. Chem. Soc. 2012, 134, 8277−8285.
24. (g) Hartmann, E.; Vyas, D. J.; Oestreich, M. Chem. Commun. 2011, 47, 7917−7932.
25. (h) Sasaki, Y.; Horita, Y.; Zhong, C.; Sawamura, M.; Ito, H. Angew. Chem., Int. Ed. 2011, 50, 2778−2782.
26. (i) Liu, B.; Gao, M.; Dang, L.; Zhao, H.; Marder, T. B.; Lin, Z. Organometallics 2012, 31, 3410−3425.
27. (j) Cid, J.; Gulyas, H.; Carbo, J. J.; Fernandez, E. Chem. Soc. Rev. 2012, 41, 3558−3570.
28. 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, 528−532.
29. (a) Ito, H.; Kubota, K. Org. Lett. 2012, 14, 890−893.
30. (b) Kubota, K.; Yamamoto, E.; Ito, H. J. Am. Chem. Soc. 2013, 135, 2635−2640.
31. (c) Iwamoto, H.; Kubota, K.; Yamamoto, E.; Ito, H. Chem. Commun. 2015, 51, 9655−9658.
32. (a) Kim, J. H.; Chung, Y. K. RSC Adv. 2014, 4, 39755−39758.
33. (b) Zhou, X.-F.; Wu, Y.-D.; Dai, J.-J.; Li, Y.-J.; Huang, Y.; Xu, H.-J. RSC Adv. 2015, 5, 46672−46676.
34. (a) Dudnik, A. S.; Fu, G. C. J. Am. Chem. Soc. 2012, 134, 10693−10697.
35. (b) Yi, J.; Liu, J.-H.; Liang, J.; Dai, J.-J.; Yang, C.-T.; Fu, Y.; Liu, L. Adv. Synth. Catal. 2012, 354, 1685−1691.
36. (c) Cheung, M. S.; Sheong, F. K.; Marder, T. B.; Lin, Z. Chem.Eur. J. 2015, 21, 7480−7488.
37. 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, 6629−6633.
38. (a) Atack, T. C.; Lecker, R. M.; Cook, S. P. J. Am. Chem. Soc. 2014, 136, 9521−9523.
39. (b) Bedford, R. B.; Brenner, P. B.; Carter, E.; Gallagher, T.; Murphy, D. M.; Pye, D. R. Organometallics 2014, 33, 5940−5943.
40. (a) Bose, S. K.; Fucke, K.; Liu, L.; Steel, P. G.; Marder, T. B. Angew. Chem., Int. Ed. 2014, 53, 1799−1803.
41. (b) Bose, S. K.; Marder, T. B. Org. Lett. 2014, 16, 4562−4565.
42. (c) Bose, S. K.; Deißenberger, A.; Eichhorn, A.; Steel, P. G.; Lin, Z.; Marder, T. B. Angew. Chem., Int. Ed. 2015, 54, 11843−11847.
43. Atack, T. C.; Cook, S. P. J. Am. Chem. Soc. 2016, 138, 6139− 6142.
44. (a) Guzman-Martinez, A.; Hoveyda, A. H. J. Am. Chem. Soc. 2010, 132, 10634−10637.
45. (b) Takemoto, Y.; Yoshida, H.; Takaki, K. Chem.Eur. J. 2012, 18, 14841−14844.
46. (c) Kobayashi, S.; Xu, P.; Endo, T.; Ueno, M.; Kitanosono, T. Angew. Chem., Int. Ed. 2012, 51, 12763−12766.
47. (d) Thorpe, S. B.; Calderone, J. A.; Santos, W. L. Org. Lett. 2012, 14, 1918−1921.
48. (e) Stavber, G.; Časar, Z. ChemCatChem 2014, 6, 2162−2174.
49. (f) Kitanosono, T.; Zhu, L.; Liu, C.; Xu, P.; Kobayashi, S. J. Am. Chem. Soc. 2015, 137, 15422−15425.
50. (g) Neeve, E. C.; Geier, S. J.; Mkhalid, I. A. I.; Westcott, S. A.; Marder, T. B. Chem. Rev. 2016, 116, 9091−9161.
51. L4 and L6 ligands were prepared on a multi-gram scale using inexpensive starting materials, see: Bantreil, X.; Nolan, S. P. Nat. Protoc. 2011, 6, 69−77.
52. (a) Endo, K.; Hirokami, M.; Shibata, T. Synlett 2009, 2009, 1331−1335.
53. (b) 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, 6342−6345.
54. (c) Xu, S.; Shangguan, X.; Li, H.; Zhang, Y.; Wang, J. J. Org. Chem. 2015, 80, 7779−7784.
55. (d) Palmer, W. N.; Obligacion, J. V.; Pappas, I.; Chirik, P. J. J. Am. Chem. Soc. 2016, 138, 766−769.
56. (e) Zhang, L.; Huang, Z. J. Am. Chem. Soc. 2015, 137, 15600−15603.
57. (a) Shi, Y.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2016, 55, 3455−3458.
58. (b) Kim, J.; Park, S.; Park, J.; Cho, S. H. Angew. Chem., Int. Ed. 2016, 55, 1498−1501.
59. (c) Joannou, M. V.; Moyer, B. S.; Meek, S. J. J. Am. Chem. Soc. 2015, 137, 6176−6179.
60. (d) Matteson, D. S.; Moody, R. J. Organometallics 1982, 1, 20−28.
61. (e) Batsanov, A. S.; Cabeza, J. A.; Crestani, M. G.; Fructos, M. R.; García-Alvarez, P.; Gille, M.; Lin, Z.; Marder, T. B. Angew. Chem., Int. Ed. 2016, 55, 4707−4710.
62. (f) Cook, A. K.; Schimler, S. D.; Matzger, A. J.; Sanford, M. S. Science 2016, 351, 1421−1424.
63. (g) Smith, K. T.; Berritt, S.; Gonzalez- Moreiras, M.; Ahn, S.; Smith, M. R., III; Baik, M.-H.; Mindiola, D. J. Science 2016, 351, 1424−1427.
64. (a) Kleeberg, C.; Dang, L.; Lin, Z.; Marder, T. B. Angew. Chem., Int. Ed. 2009, 48, 5350−5354.
65. (b) Yang, C.-T.; Zhang, Z.-Q.; Liu, Y.C.; Liu, L. Angew. Chem., Int. Ed. 2011, 50, 3904−3907.
66. Hawker, C. J.; Barclay, G. G.; Orellana, A.; Dao, J.; Devonport, W. Macromolecules 1996, 29, 5245−5254.