Metal-free carbonylations by photoredox catalysis

Angewandte Chemie - International Edition

Volumn 54, Issue 7, 2015, Pages 2270-2274

  Majek, Michal ^a   Von Wangelin, Axel Jacobi ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Carbonylation; Esters; Organocatalysis; Photoredox catalysis; Redox reaction; Visible light

Indexed keywords

CARBON; CARBON MONOXIDE; CATALYSIS; ESTERIFICATION; ESTERS; INDUSTRIAL RESEARCH; LIGANDS; LIGHT; PALLADIUM; REACTION KINETICS; REDOX REACTIONS; SYNTHESIS (CHEMICAL);

ALTERNATIVE PROCEDURES; ARYL ELECTROPHILES; CARBONYLATION REACTIONS; INDUSTRIAL PROCESSS; ORGANOCATALYSIS; PHOTOREDOX CATALYSIS; RADICAL TRAPPING; VISIBLE LIGHT;

CARBONYLATION;

ALCOHOL DERIVATIVE; BENZOIC ACID DERIVATIVE; CARBON MONOXIDE; DIAZONIUM COMPOUND; EOSIN; ESTER;

ALKYLATION; CATALYSIS; CHEMISTRY; LIGHT; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; SYNTHESIS;

ALCOHOLS; ALKYLATION; BENZOATES; CARBON MONOXIDE; CATALYSIS; DIAZONIUM COMPOUNDS; EOSINE YELLOWISH-(YS); ESTERS; LIGHT; OXIDATION-REDUCTION; PHOTOCHEMICAL PROCESSES;

EID: 84922295534     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201408516     Document Type: Article

References (60)

1. W. Riemenschneider, H. M. Bolt in Ullmann's Encyclopedia of Industrial Chemistry, Vol. 13, Wiley-VCH, Weinheim, 2005, p. 245.
2. nd ed., Wiley-VCH, Weinheim, 2010.
3. A. Brennführer, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 2009, 48, 4114;
4. Angew. Chem. 2009, 121, 4176.
5. J. Magano, J. R. Dunetz, Chem. Rev. 2011, 111, 2177;
6. H. M. Colquhoun, D. J. Thompson, M. V. Twigg, Carbonylation. Direct Synthesis of Carbonyl Compounds, Plenum, New York, 1991.
7. A. Roglans, A. Pla-Quintana, M. Moreno-Manas, Chem. Rev. 2006, 106, 4622.
8. J. C. Clark, R. C. Cookson, J. Chem. Soc. 1962, 686;
9. K. Kikukawa, K. Kono, K. Nagira, F. Wada, T. Matsuda, J. Org. Chem. 1981, 46, 4413;
10. S. Sengupta, S. K. Sadhukhan, S. Bhattacharyya, J. Guha, J. Chem. Soc. Perkin Trans. 1 1998, 407.
11. C. F. J. Barnard, Organometallics 2008, 27, 5402.
12. A. N. Abeywickrema, A. L. J. Beckwith, J. Org. Chem. 1987, 52, 2568.
13. P. Allongue, M. Delamar, B. Desbat, O. Fagebaume, R. Hitmi, J. Pinson, J.-M. Saveant, J. Am. Chem. Soc. 1997, 119, 201;
14. C. Combellas, D.-E. Jiang, F. Kanoufi, J. Pinson, F. I. Podvorica, Langmuir 2009, 25, 286.
15. J. M. R. Narayanam, C. R. J. Stephenson, Chem. Soc. Rev. 2011, 40, 102;
16. K. Zeitler, Angew. Chem. Int. Ed. 2009, 48, 9785;
17. Angew. Chem. 2009, 121, 9969;
18. D. M. Schultz, T. P. Yoon, Science 2014, 343, 985;
19. d) D. Ravelli, S. Protti, M. Fagnoni, A. Albini, Curr. Org. Chem. 2013, 17, 2366.
20. D. Kalyani, K. B. McMurtrey, S. R. Neufeldt, M. S. Sanford, J. Am. Chem. Soc. 2011, 133, 18566;
21. D. P. Hari, P. Schroll, B. König, J. Am. Chem. Soc. 2012, 134, 2958;
22. B. Sahoo, M. N. Hopkinson, F. Glorius, J. Am. Chem. Soc. 2013, 135, 5505.
23. C. K. Prier, D. A. Rankic, D.W. C. MacMillan, Chem. Rev. 2013, 113, 5322; Ir:
24. A. Noble,D.W. C. MacMillan, J. Am. Chem. Soc. 2014, 136, 11602;
25. M. T. Pirnot, D. A. Rankic, D. B. C. Martin, D.W. C. MacMillan, Science 2013, 339, 1593;
26. S. Zhu, A. Das, L. Bui, H. Zhou, D. P. Curran, M. Rueping, J. Am. Chem. Soc. 2013, 135, 1823; Cu:
27. M. Majek, A. Jacobi vonWangelin, Angew. Chem. Int. Ed. 2013, 52, 5919;
28. Angew. Chem. 2013, 125, 6033;
29. M. Pirtsch, S. Paria, T. Matsuno, H. Isobe, O. Reiser, Chem. Eur. J. 2012, 18, 7336.
30. G. B. Deacon, J. M. Patrick, B.W. Skelton, N. C. Thomas, A. H. White, Aust. J. Chem. 1984, 37, 929.
31. D. A. Nicewicz, T. M. Nguyen, ACS Catal. 2014, 4, 355;
32. D. P. Hari, B. König, Chem. Commun. 2014, 50, 6688;
33. D. Ravelli, M. Fagnoni, A. Albini, Chem. Soc. Rev. 2013, 42, 97.
34. M. Okada, T. Fukuyama, K. Yamada, I. Ryu, D. Ravelli, M. Fagnoni, Chem. Sci. 2014, 5, 2893;
35. I. Ryu, A. Tani, T. Fukuyama, D. Ravelli, M. Fagnoni, A. Albini, Angew. Chem. Int. Ed. 2011, 50, 1869;
36. Angew. Chem. 2011, 123, 1909.
37. H.-C. Lu, H.-K. Chen, B.-M. Cheng, Y.-P. Kuo, J. F. Ogilvie, J. Phys. B 2005, 38, 3693.
38. D. P. Hari, B. König, Angew. Chem. Int. Ed. 2013, 52, 4734;
39. Angew. Chem. 2013, 125, 4832.
40. M. Majek, A. Jacobi vonWangelin, Chem. Commun. 2013, 49, 5507.
41. L. Benati, R. Leardini, M. Minozzi, D. Nanni, R. Scialpi, P. Spagnolo, S. Strazzari, G. Zanardi, Angew. Chem. Int. Ed. 2004, 43, 3598;
42. Angew. Chem. 2004, 116, 3682.
43. X. Wang, G. D. Cuny, T. Noel, Angew. Chem. Int. Ed. 2013, 52, 7860;
44. Angew. Chem. 2013, 125, 8014.
45. T.W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley, New York, 1999 ;
46. a thermal radical carbonylation of Ar-I with KOtBu: H. Zhang, R. Shi, A. Ding, L. Lu, B. Chen, A. Lei, Angew. Chem. Int. Ed. 2012, 51, 12542;
47. Angew. Chem. 2012, 124, 12710.
48. R. Stanley, Paint Coat. Ind. 2001, 17, 68.
49. E. Zipfel, J.-R. Grezes, W. Seiffert, H.W. Zimmermann, Histochemistry 1982, 75, 539.
50. E. Forgacs, T. Cserhati, G. Oros, Environ. Int. 2004, 30, 953.
51. E. S. Lewis, J. M. Insole, J. Am. Chem. Soc. 1964, 86, 32.
52. M. Majek, F. Filace, A. Jacobi vonWangelin, Beilstein J. Org. Chem. 2014, 10, 981.
53. C. Chatgilialoglu, D. Crich, M. Komatsu, I. Ryu, Chem. Rev. 1999, 99, 1992;
54. I. Ryu, Chem. Soc. Rev. 2001, 30, 16;
55. S. Sumino, A. Fusano, H. Okai, T. Fukuyama, I. Ryu, Beilstein J. Org. Chem. 2014, 10, 150;
56. T. Kawamoto, T. Okada, D. P. Curran, I. Ryu, Org. Lett. 2013, 15, 2144;
57. A. Fusano, S. Sumino, S. Nishitani, T. Inoue, K. Morimoto, T. Fukuyama, I. Ryu, Chem. Eur. J. 2012, 18, 9415.
58. M.-H. Baik, R. A. Friesner, J. Phys. Chem. A 2002, 106, 7407;
59. Y. Fu, L. Liu, H.-Z. Yu, Y.-M.Wang, Q.-X. Guo, J. Am. Chem. Soc. 2005, 127, 7227.
60. M. Tanaka, M. Fujiwara,Q. Xu, Y. Souma, H. Ando, K. K. Laali, J. Am. Chem. Soc. 1997, 119, 5100.