Photoredox/Brønsted Acid Co-Catalysis Enabling Decarboxylative Coupling of Amino Acid and Peptide Redox-Active Esters with N-Heteroarenes

ACS Catalysis

Volumn 7, Issue 1, 2017, Pages 907-911

  Cheng, Wan Min ^a   Shang, Rui ^a,b   Fu, Yao ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

decarboxylation; N (acyloxy)phthalimide; N heteroarenes; photoredox catalysis; aminoalkylation

Indexed keywords

AMINO ACIDS; CARBOXYLATION; CATALYSIS; CATALYSTS; ESTERS; PEPTIDES; SUBSTRATES;

DECARBOXYLATION; DECARBOXYLATIVE COUPLINGS; ELECTRON DEFICIENCY; HETEROARENES; MEDICINAL APPLICATIONS; N-HYDROXYPHTHALIMIDE; PHOTOREDOX CATALYSIS; PHTHALIMIDE;

REDOX REACTIONS;

EID: 85017796310     PISSN: None     EISSN: 21555435     Source Type: Journal    
DOI: 10.1021/acscatal.6b03215     Document Type: Article

References (57)

1. Duncton, M. A. J. MedChemComm 2011, 2, 1135-1161 10.1039/c1md00134e
2. Nagib, D. A.; MacMillan, D. W. C. Nature 2011, 480, 224-228 10.1038/nature10647
3. Minisci, F.; Bernardi, R.; Bertini, F.; Galli, R.; Perchinummo, M. Tetrahedron 1971, 27, 3575-3579 10.1016/S0040-4020(01)97768-3
4. Minisci, F.; Vismara, E.; Fontana, F. Heterocycles 1989, 28, 489-519 10.3987/REV-88-SR1
5. Fujiwara, Y.; Domingo, V.; Seiple, I. B.; Gianatassio, R.; Del Bel, M.; Baran, P. S. J. Am. Chem. Soc. 2011, 133, 3292-3295 10.1021/ja111152z
6. Molander, G. A.; Colombel, V.; Braz, V. A. Org. Lett. 2011, 13, 1852-1855 10.1021/ol2003572
7. Fujiwara, Y.; Dixon, J. A.; O'Hara, F.; Funder, E. D.; Dixon, D. D.; Rodriguez, R. A.; Baxter, R. D.; Herle, B.; Sach, N.; Collins, M. R.; Ishihara, Y.; Baran, P. S. Nature 2012, 492, 95-99 10.1038/nature11680
8. Antonchick, A. P.; Burgmann, L. Angew. Chem., Int. Ed. 2013, 52, 3267-3271 10.1002/anie.201209584
9. Miyake, Y.; Nakajima, K.; Nishibayashi, Y. Chem.-Eur. J. 2012, 18, 16473-16477 10.1002/chem.201203066
10. Miyake, Y.; Nakajima, K.; Nishibayashi, Y. J. Am. Chem. Soc. 2012, 134, 3338-3341 10.1021/ja211770y
11. Nakajima, K.; Miyake, Y.; Nishibayashi, Y. Acc. Chem. Res. 2016, 49, 1946-1956 10.1021/acs.accounts.6b00251
12. Khan, M. T. H. Bioactive heterocycles V, Vol 11, 2007. In Topics in Heterocyclic Chemistry; Gupta, R. R., Ed.; Springer Verlag: New York, 2008.
13. Blaskovich, M. A. Handbook on Syntheses of Amino Acids: General Routes for the Syntheses of Amino Acids, 1 st ed.; Oxford University Press: New York, 2010.
14. Cowden, C. J. Org. Lett. 2003, 5, 4497-4499 10.1021/ol035814+
15. Mai, D. N.; Baxter, R. D. Org. Lett. 2016, 18, 3738-3741 10.1021/acs.orglett.6b01754
16. Allen, L. J.; Cabrera, P. J.; Lee, M.; Sanford, M. S. J. Am. Chem. Soc. 2014, 136, 5607-5610 10.1021/ja501906x
17. Pratsch, G.; Lackner, G. L.; Overman, L. E. J. Org. Chem. 2015, 80, 6025-6036 10.1021/acs.joc.5b00795
18. Toriyama, F.; Cornella, J.; Wimmer, L.; Chen, T.-G.; Dixon, D. D.; Creech, G.; Baran, P. S. J. Am. Chem. Soc. 2016, 138, 11132-11135 10.1021/jacs.6b07172
19. Wang, J.; Qin, T.; Chen, T.-G.; Wimmer, L.; Edwards, T. J.; Cornella, J.; Vokits, B.; Shaw, S. A.; Baran, P. S. Angew. Chem., Int. Ed. 2016, 55, 9676-9679 10.1002/anie.201605463
20. Huihui, K. M. M.; Caputo, J. A.; Melchor, Z.; Olivares, A. M.; Spiewak, A. M.; Johnson, K. A.; DiBenedetto, T. A.; Kim, S.; Ackerman, L. K. G.; Weix, D. J. J. Am. Chem. Soc. 2016, 138, 5016-5019 10.1021/jacs.6b01533
21. Qin, T.; Cornella, J.; Li, C.; Malins, L.; Edwards, J. T.; Kawamura, S.; Maxwell, B. D.; Eastgate, M. D.; Baran, P. S. Science 2016, 352, 801-805 10.1126/science.aaf6123
22. Cornella, J.; Edwards, J. T.; Qin, T.; Kawamura, S.; Wang, J.; Pan, C.-M.; Gianatassio, R.; Schmidt, M.; Eastgate, M. D.; Baran, P. S. J. Am. Chem. Soc. 2016, 138, 2174-2177 10.1021/jacs.6b00250
23. Schwarz, J.; König, B. Green Chem. 2016, 18, 4743-4749 10.1039/C6GC01101B
24. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322-5363 10.1021/cr300503r
25. Schultz, D. M.; Yoon, T. P. Science 2014, 343, 1239176 10.1126/science.1239176
26. Xuan, J.; Zhang, Z. G.; Xiao, W. J. Angew. Chem., Int. Ed. 2015, 54, 15632-15641 10.1002/anie.201505731
27. Chen, J. R.; Hu, X. Q.; Lu, L. Q.; Xiao, W. J. Acc. Chem. Res. 2016, 49, 1911-1923 10.1021/acs.accounts.6b00254
28. Zuo, Z. W.; Ahneman, D. T.; Chu, L. L.; Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345, 437-440 10.1126/science.1255525
29. Tellis, J. C.; Primer, D. N.; Molander, G. A. Science 2014, 345, 433-436 10.1126/science.1253647
30. Zhou, Q. Q.; Guo, W.; Ding, W.; Wu, X.; Chen, X.; Lu, L. Q.; Xiao, W. J. Angew. Chem., Int. Ed. 2015, 54, 11196-11199 10.1002/anie.201504559
31. Uraguchi, D.; Kinoshita, N.; Kizu, T.; Ooi, T. J. Am. Chem. Soc. 2015, 137, 13768-13771 10.1021/jacs.5b09329
32. Kizu, T.; Uraguchi, D.; Ooi, T. J. Org. Chem. 2016, 81, 6953-6958 10.1021/acs.joc.6b00445
33. Fava, E.; Millet, A.; Nakajima, M.; Loescher, S.; Rueping, M. Angew. Chem., Int. Ed. 2016, 55, 6776-6779 10.1002/anie.201511235
34. Akiyama, T.; Mori, K. Chem. Rev. 2015, 115, 9277-9306 10.1021/acs.chemrev.5b00041
35. Skubi, K. L.; Blum, T. R.; Yoon, T. P. Chem. Rev. 2016, 116, 10035-10074 10.1021/acs.chemrev.6b00018
36. Zuo, Z.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 5257-5260 10.1021/ja501621q
37. Primer, D. N.; Karakaya, I.; Tellis, J. C.; Molander, G. A. J. Am. Chem. Soc. 2015, 137, 2195-2198 10.1021/ja512946e
38. Terrett, J. A.; Cuthbertson, J. D.; Shurtleff, V. W.; MacMillan, D. W. C. Nature 2015, 524, 330-334 10.1038/nature14875
39. Cheng, W.-M.; Shang, R.; Yu, H.-Z.; Fu, Y. Chem.-Eur. J. 2015, 21, 13191-13195 10.1002/chem.201502286
40. Wang, G.-Z.; Shang, R.; Cheng, W.-M.; Fu, Y. Org. Lett. 2015, 17, 4830-4833 10.1021/acs.orglett.5b02392
41. El Khatib, M.; Serafim, R. A. M.; Molander, G. A. Angew. Chem., Int. Ed. 2016, 55, 254-258 10.1002/anie.201506147
42. Joe, C. L.; Doyle, A. G. Angew. Chem., Int. Ed. 2016, 55, 4040-4043 10.1002/anie.201511438
43. Shaw, M. H.; Shurtleff, V. W.; Terrett, J. A.; Cuthbertson, J. D.; MacMillan, D. W. C. Science 2016, 352, 1304-1308 10.1126/science.aaf6635
44. Johnston, C. P.; Smith, R. T.; Allmendinger, S.; MacMillan, D. W. C. Nature 2016, 536, 322-325 10.1038/nature19056
45. Tarantino, K. T.; Liu, P.; Knowles, R. R. J. Am. Chem. Soc. 2013, 135, 10022-10025 10.1021/ja404342j
46. Rono, L. J.; Yayla, H. G.; Wang, D. Y.; Armstrong, M. F.; Knowles, R. R. J. Am. Chem. Soc. 2013, 135, 17735-17738 10.1021/ja4100595
47. Kaur, H.; Kamalov, M.; Brimble, M. A. Acc. Chem. Res. 2016, 49, 2199-2208 10.1021/acs.accounts.6b00366
48. DiRocco, D. A.; Dykstra, K.; Krska, S.; Vachal, P.; Conway, D. V.; Tudge, M. Angew. Chem., Int. Ed. 2014, 53, 4802-4806 10.1002/anie.201402023
49. Jin, J.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2015, 54, 1565-1569 10.1002/anie.201410432
50. Jin, J.; MacMillan, D. W. C. Nature 2015, 525, 87-90 10.1038/nature14885
51. Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075-10166 10.1021/acs.chemrev.6b00057
52. Radicals in Organic Synthesis; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; pp 229-249.
53. Shaw, M. H.; Twilton, J.; MacMillan, D. W. C. J. Org. Chem. 2016, 81, 6898-6926 10.1021/acs.joc.6b01449
54. Li, G.-X.; Morales-Rivera, C. A.; Wang, Y. X.; Gao, F.; He, G.; Liu, P.; Chen, G. Chem. Sci. 2016, 7, 6407-6412 10.1039/C6SC02653B
55. McCallum, T.; Barriault, L. Chem. Sci. 2016, 7, 4754-4758 10.1039/C6SC00807K
56. Wu, B.; Wijma, H. J.; Song, L.; Rozeboom, H. J.; Poloni, C.; Tian, Y.; Arif, M. I.; Nuijens, T.; Quaedflieg, P. J. L. M.; Szymanski, W.; Feringa, B. L.; Janssen, D. B. ACS Catal. 2016, 6, 5405-5414 10.1021/acscatal.6b01062
57. Jin, Y.; Jiang, M.; Wang, H.; Fu, H. Sci. Rep. 2016, 6, 20068 10.1038/srep20068