Visible-Light-Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ-Amino Boronic Esters

Angewandte Chemie - International Edition

Volumn 57, Issue 8, 2018, Pages 2155-2159

  Noble, Adam ^a   Mega, Riccardo S ^a   Pflästerer, Daniel ^a   Myers, Eddie L ^a   Aggarwal, Varinder K ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

amino acids; boron; photochemistry; radical reactions; reaction mechanisms

Indexed keywords

AMINO ACIDS; BORON; CARBOXYLIC ACIDS; PHOTOCHEMICAL REACTIONS; REACTION INTERMEDIATES; REACTION KINETICS;

ALKYL CARBOXYLIC ACIDS; BORON-CONTAINING; BORONIC ESTERS; PHOTOREDOX CATALYSIS; RADICAL ADDITION; RADICAL REACTIONS; REACTION MECHANISM; SINGLE ELECTRON REDUCTION;

ESTERS;

EID: 85041024040     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201712186     Document Type: Article

References (59)

1. Boronic Acids: Preparation and Applications in Organic Synthesis Medicine and Materials, Vols. 1 and 2 (Ed.: D. G. Hall), Wiley-VCH, Weinheim, 2011.
2. A. Suzuki, Angew. Chem. Int. Ed. 2011, 50, 6722–6737;
3. Angew. Chem. 2011, 123, 6854–6869;
4. D. Leonori, V. K. Aggarwal, Angew. Chem. Int. Ed. 2015, 54, 1082–1096;
5. Angew. Chem. 2015, 127, 1096–1111;
6. C. Sandford, V. K. Aggarwal, Chem. Commun. 2017, 53, 5481–5494; For use in Lewis acid catalysis, see:
7. E. Dimitrijević, M. S. Taylor, ACS Catal. 2013, 3, 945–962;
8. H. Zheng, D. G. Hall, Aldrichimica Acta 2014, 47, 41–51.
9. W. L. A. Brooks, B. S. Sumerlin, Chem. Rev. 2016, 116, 1375–1397.
10. S. D. Bull, M. G. Davidson, J. M. H. Ven Den Elsen, J. S. Fossey, A. T. A. Jenkins, Y.-B. Jiang, Y. Kubo, F. Marken, K. Sakurai, J. Zhao, T. D. James, Acc. Chem. Res. 2013, 46, 312–326;
11. G. F. Whyte, R. Vilar, R. Woscholski, J. Chem. Biol. 2013, 6, 161–174.
12. W. Yang, X. Gao, B. Wang, Med. Res. Rev. 2003, 23, 346–368;
13. P. C. Trippier, C. McGuigan, MedChemComm 2010, 1, 183–198;
14. C. Ballatore, D. M. Huryn, A. B. Smith III, ChemMedChem 2013, 8, 385–395;
15. D. B. Diaz, A. K. Yudin, Nat. Chem. 2017, 9, 731–742.
16. D. S. Matteson, Med. Res. Rev. 2008, 28, 233–246;
17. R. Smoum, A. Rubinstein, V. M. Dembitsky, M. Srebnik, Chem. Rev. 2012, 112, 4156–4220.
18. M. Ordóñez, C. Cativiela, Tetrahedron: Asymmetry 2007, 18, 3–99;
19. K. Gajcy, S. Lochynski, T. Librowski, Curr. Med. Chem. 2010, 17, 2338–2347.
20. For examples of bioactive γ-amino boronic acid derivatives, see:
21. M. J. Luderer, et al., Pharm. Res. 2016, 33, 2530–2539;
22. A. Maynard, et al., J. Med. Chem. 2014, 57, 1902–1913;
23. L. L. Johnson, Jr., T. A. Houston, Tetrahedron Lett. 2002, 43, 8905;
24. C. P. Decicco, et al., Bioorg. Med. Chem. Lett. 2001, 11, 2561–2564.
25. For a recent investigation into β-amino boronic acids, see: J. Tan, A. B. Cognetta III, D. B. Diaz, K. M. Lum, S. Adachi, S. Kundu, B. F. Cravatt, A. K. Yudin, Nat. Commun. 2017, 8, 1760.
26. For radical additions to vinyl boronic esters, see:
27. D. S. Matteson, J. Am. Chem. Soc. 1959, 81, 5004–5005;
28. D. S. Matteson, J. Am. Chem. Soc. 1960, 82, 4228–4233;
29. D. S. Matteson, G. D. Shaumberg, J. Org. Chem. 1966, 31, 726–731;
30. N. Guennouni, F. Lhermitte, S. Cochard, B. Carboni, Tetrahedron 1995, 51, 6999–7018;
31. E. Lee, K. Zong, H. Y. Kang, J. Lim, J. Y. Kim, Bull. Korean Chem. Soc. 2000, 21, 765–766;
32. H. Lopez-Ruiz, S. Z. Zard, Chem. Commun. 2001, 2618–2619;
33. M. R. Heinrich, L. A. Sharp, S. Z. Zard, Chem. Commun. 2005, 3077–3079.
34. For radical additions to vinyl boronate complexes, see:
35. B. Quiclet-Sire, S. Z. Zard, J. Am. Chem. Soc. 2015, 137, 6762–6765;
36. M. Kischkewitz, K. Okamoto, C. Mück-Lichtenfeld, A. Studer, Science 2017, 355, 936–938;
37. M. Silvi, C. Sandford, V. K. Aggarwal, J. Am. Chem. Soc. 2017, 139, 5736–5739;
38. G. J. Lovinger, J. P. Morken, J. Am. Chem. Soc. 2017, 139, 17293–17296.
39. For radical additions to vinyl boronate complexes with regioselectivity for addition α to boron, see:
40. H. Kim, D. W. C. MacMillan, J. Am. Chem. Soc. 2008, 130, 398–399;
41. Y. Yasu, T. Koike, M. Akita, Chem. Commun. 2013, 49, 2037–2039;
42. D. Fernandez Reina, A. Ruffoni, Y. S. S. Al-Faiyz, J. J. Douglas, N. S. Sheikh, D. Leonori, ACS Catal. 2017, 7, 4126–4130.
43. For selected reviews on photoredox catalysis, see:
44. C. K. Prier, D. A. Rankic, D. W. C. MacMillan, Chem. Rev. 2013, 113, 5322–5363;
45. M. H. Shaw, J. Twilton, D. W. C. MacMillan, J. Org. Chem. 2016, 81, 6898–6926;
46. J. W. Tucker, C. R. J. Stephenson, J. Org. Chem. 2012, 77, 1617–1622;
47. D. M. Schultz, T. P. Yoon, Science 2014, 343, 1239176.
48. L. Chu, C. Ohta, Z. Zuo, D. W. C. MacMillan, J. Am. Chem. Soc. 2014, 136, 10886–10889;
49. S. Bloom, C. Liu, D. K. Kölmel, J. X. Qiao, Y. Zhang, M. A. Poss, W. R. Ewing, D. W. C. MacMillan, Nat. Chem. 2018, DOI: https://doi.org/10.1038/nchem.2888; For related examples, see:
50. Y. Miyake, K. Nakajima, Y. Nishibayashi, Chem. Commun. 2013, 49, 7854–7856;
51. A. Millet, Q. Lefebvre, M. Rueping, Chem. Eur. J. 2016, 22, 13464–13468;
52. N. P. Ramirez, J. C. Gonzalez-Gomez, Eur. J. Org. Chem. 2017, 2154–2163.
53. See the Supporting Information for details.
54. H. Uoyama, K. Goushi, K. Shizu, H. Nomura, C. Adachi, Nature 2012, 492, 234–238.
55. S. Ladouceur, D. Fortin, E. Zysman-Colman, Inorg. Chem. 2011, 50, 11514–11526.
56. The generation of the α-boryl anion 50 should be facilitated by the stabilizing effect the tricoordinate boron atom has on the adjacent carbanion. See: K. Hong, X. Lin, J. P. Morken, J. Am. Chem. Soc. 2014, 136, 10581–10584.
57. Y. Fu, L. Liu, H. Yu, Y. Wang, Q. Guo, J. Am. Chem. Soc. 2005, 127, 7227–7234; See also:
58. H. G. Roth, N. A. Romero, D. A. Nicewicz, Synlett 2016, 27, 714–723.
59. Attempts to measure this reduction potential by cyclic voltammetry using a model α-iodo boronic ester showed only a single irreversible reduction peak at −2.0 V vs. SCE in MeCN, corresponding to the two-electron reduction process. See the Supporting Information for details.