Photocatalytic Radical Alkylation of Electrophilic Olefins by Benzylic and Alkylic Zinc-Sulfinates

ACS Catalysis

Volumn 7, Issue 8, 2017, Pages 5357-5362

  Gualandi, Andrea ^a   Mazzarella, Daniele ^a,c   Ortega Martínez, Aitor ^a,d   Mengozzi, Luca ^a   Calcinelli, Fabio ^a   Matteucci, Elia ^a   Monti, Filippo ^b   Armaroli, Nicola ^b   Sambri, Letizia ^a   Cozzi, Pier Giorgio ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b Istituto Per La Sintesi Organica E La Fotoreattività   (Italy)

^c INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^d UNIVERSITY OF ALICANTE   (Spain)

Author keywords

alkylation; benzylation; iridium catalyst; photocatalysis; sulfinates

Indexed keywords

ALKYLATION; OLEFINS; PHOTOCATALYSIS; ZINC;

BENZYLATION; IRIDIUM CATALYST; IRIDIUM COMPLEX; MICHAEL ACCEPTORS; PHOTO-CATALYTIC; PHOTOCATALYTIC OXIDATIONS; SULFINATES; SULFONYLATION REACTIONS;

IRIDIUM COMPOUNDS;

EID: 85027258707     PISSN: None     EISSN: 21555435     Source Type: Journal    
DOI: 10.1021/acscatal.7b01669     Document Type: Article

References (63)

1. Borsche, W.; Lange, W. Ber. Dtsch. Chem. Ges. 1906, 39, 2346-2356 10.1002/cber.190603902212
2. Smiles, S.; Le Rossignol, R. J. Chem. Soc., Trans. 1908, 93, 745-762 10.1039/CT9089300745
3. For a review, see: Aziz, J.; Messaoudi, S.; Alami, M.; Hamze, A. Org. Biomol. Chem. 2014, 12, 9743-9759 10.1039/C4OB01727G
4. O'Hara, F.; Baxter, R. D.; O'Brien, A. G.; Collins, M. R.; Dixon, J. A.; Fujiwara, Y.; Ishihara, Y.; Baran, P. S. Nat. Protoc. 2013, 8, 1042-1047 10.1038/nprot.2013.059
5. Wu, W. Q.; Yi, S. J.; Yu, Y.; Huang, W.; Jiang, H. F. J. Org. Chem. 2017, 82, 1224-1230 10.1021/acs.joc.6b02416
6. 1/2 = + 1.16 vs SCE; see: Galicia, M.; Gonzalez, F. J. J. Electrochem. Soc. 2002, 149, D46-D50 10.1149/1.1450616
7. 1/2 = + 0.45 V vs SCE; see: Meyer, A. U.; Strakova, K.; Slanina, T.; König, B. Chem.-Eur. J. 2016, 22, 8694-8699 10.1002/chem.201601000
8. Chatgilialoglu, C.; Lunazzi, L.; Ingold, K. U. J. Org. Chem. 1983, 48, 3588-3589 10.1021/jo00168a053
9. Studer, A.; Curran, D. P. Angew. Chem., Int. Ed. 2016, 55, 58-102 10.1002/anie.201505090
10. Yan, M.; Lo, J. C.; Edwards, J. T.; Baran, P. S. J. J. Am. Chem. Soc. 2016, 138, 12692-12714 10.1021/jacs.6b08856
11. Yan, M.; Lo, J. C.; Edwards, J. T.; Baran, P. S. J. Am. Chem. Soc. 2016, 138, 12692-12714 10.1021/jacs.6b08856
12. Ji, Y.; Brueckl, T.; Baxter, R. D.; Fujiwara, Y.; Seiple, I. B.; Su, S.; Blackmond, D. G.; Baran, P. S. Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 14411-14415 10.1073/pnas.1109059108
13. Fujiwara, Y.; Dixon, J. A.; Rodriguez, R. A.; Baxter, R. D.; Dixon, D. D.; Collins, M. R.; Blackmond, D. G.; Baran, P. S. J. Am. Chem. Soc. 2012, 134, 1494-1497 10.1021/ja211422g
14. Fujiwara, Y.; Dixon, J. A.; O'Hara, F.; Funder, E. D.; Dixon, D. D.; Rodriguez, R. A.; Baxter, R. D.; Herlé, B.; Sach, N.; Collins, M. R.; Ishihara, Y.; Baran, P. S. Nature 2012, 492, 95-99 10.1038/nature11680
15. Zhou, Q.; Ruffoni, A.; Gianatassio, R.; Fujiwara, Y.; Sella, E.; Shabat, D.; Baran, P. S. Angew. Chem., Int. Ed. 2013, 52, 3949-3952 10.1002/anie.201300763
16. O'Hara, F.; Blackmond, D. G.; Baran, P. S. J. Am. Chem. Soc. 2013, 135, 12122-12134 10.1021/ja406223k
17. Zhou, Q.; Gui, J.; Pan, C.-M.; Albone, E.; Cheng, X.; Suh, E. M.; Grasso, L.; Ishihara, Y.; Baran, P. S. J. Am. Chem. Soc. 2013, 135, 12994-12997 10.1021/ja407739y
18. Gui, J.; Zhou, Q.; Pan, C.-M.; Yabe, Y.; Burns, A. C.; Collins, M. R.; Ornelas, M. A.; Ishihara, Y.; Baran, P. S. J. Am. Chem. Soc. 2014, 136, 4853-4856 10.1021/ja5007838
19. Flegeau, E. F.; Harrison, J. M.; Willis, M. C. Synlett 2016, 27, 101-105 10.1055/s-0035-1560578
20. Emmett, E. J.; Willis, M. C. Asian J. Org. Chem. 2015, 4, 602-611 10.1002/ajoc.201500103
21. Deeming, A. S.; Russell, C. J.; Willis, M. C. Angew. Chem., Int. Ed. 2015, 54, 1168-1171 10.1002/anie.201409283
22. Deeming, A. S.; Emmett, E. J.; Richards-Taylor, C. S.; Willis, M. C. Synthesis 2014, 46, 2701-2710 10.1055/s-0034-1379042
23. Deeming, A. S.; Russell, C. J.; Hennessy, A. J.; Willis, M. C. Org. Lett. 2014, 16, 150-153 10.1021/ol403122a
24. Richards-Taylor, C. S.; Blake-more, D. C.; Willis, M. C. Chem. Sci. 2014, 5, 222-228 10.1039/C3SC52332B
25. Minisci, F.; Fontana, F.; Vismara, E. J. Heterocycl. Chem. 1990, 27, 79-96 10.1002/jhet.5570270107
26. Ni, C.; Hu, M.; Hu, J. Chem. Rev. 2015, 115, 765-825 10.1021/cr5002386
27. Meesin, J.; Katrun, P.; Pareseecharoen, C.; Pohmakotr, M.; Reutrakul, V.; Soorukram, D.; Kuhakarn, C. J. Org. Chem. 2016, 81, 2744-2752 10.1021/acs.joc.5b02810
28. Li, Z.; Cui, Z.; Liu, Z.-Q. Org. Lett. 2013, 15, 406-409 10.1021/ol3034059
29. Meyer, A. U.; Jäger, S.; Hari, D. P.; König, B. Adv. Synth. Catal. 2015, 357, 2050-2054 10.1002/adsc.201500142
30. Meyer, A. U.; Lau, V. W. H.; König, B.; Lotsch, B. V. Eur. J. Org. Chem. 2017, 2017, 2179-2185 10.1002/ejoc.201601637
31. Hering, T.; Meyer, A. U.; König, B. J. Org. Chem. 2016, 81, 6927-6936 and references therein. 10.1021/acs.joc.6b01050
32. Giese, B.; Gonzalez-Gomez, J. A.; Witzel, T. Angew. Chem., Int. Ed. Engl. 1984, 23, 69-70 10.1002/anie.198400691
33. Qin, T.; Malins, L. R.; Edwards, J. T.; Merchant, R. R.; Novak, A. J. E.; Zhong, J. Z.; Mills, R. B.; Yan, M.; Yuan, C.; Eastgate, M. D.; Baran, P. S. Angew. Chem. 2017, 129, 266 10.1002/ange.201609662
34. Miyake, Y.; Nakajima, K.; Nishibayashi, Y. Chem. Commun. 2013, 49, 7854-7856 10.1039/c3cc44438d
35. Capaldo, L.; Buzzetti, L.; Merli, D.; Fagnoni, M.; Ravelli, D. J. Org. Chem. 2016, 81, 7102-7109 10.1021/acs.joc.6b00984
36. Silvi, M.; Verrier, C.; Rey, R. Y.; Buzzetti, L.; Melchiorre, P. Nat. Chem. 2017, 10.1038/nchem.2748
37. Zhou, R.; Liu, H.; Tao, H.; Yu, Y.; Wu, J. Chem. Sci. 2017, 8, 4654-4659 10.1039/C7SC00953D
38. Gualandi, A.; Marchini, M.; Mengozzi, L.; Natali, M.; Lucarini, M.; Ceroni, P.; Cozzi, P. G. ACS Catal. 2015, 5, 5927-5931 10.1021/acscatal.5b01573
39. Magagnano, G.; Gualandi, A.; Marchini, M.; Mengozzi, L.; Ceroni, P.; Cozzi, P. G. Chem. Commun. 2017, 53, 1591-1594 10.1039/C6CC09387F
40. Gualandi, A.; Matteucci, E.; Monti, F.; Baschieri, A.; Armaroli, N.; Sambri, L.; Cozzi, P. G. Chem. Sci. 2017, 8, 1613-1620 10.1039/C6SC03374A
41. Chang, P.; Yeh, P.; Chen, H. G.; Knochel, P. Org. Synth. 1992, 70, 195-202 10.15227/orgsyn.070.0195
42. Fukuzumi, S.; Kotani, H.; Ohkubo, K.; Ogo, S.; Tkachenko, N. V.; Lemmetyinen, H. J. Am. Chem. Soc. 2004, 126, 1600-1601 10.1021/ja038656q
43. Lowry, M. S.; Goldsmith, J. I.; Slinker, J. D.; Rohl, R.; Pascal, R. A.; Malliaras, G. G.; Bernhard, S. Chem. Mater. 2005, 17, 5712-5719 10.1021/cm051312+
44. For coordination of zinc sulfonates with a nitrogen-containing heterocycle, see: Lindner, E.; Frembs, D. W. R.; Krug, D. Chem. Ber. 1975, 108, 291-300 10.1002/cber.19751080137
45. Chen, Q.; Mayer, P.; Mayr, H. Angew. Chem., Int. Ed. 2016, 55, 12664 10.1002/anie.201601875
46. Allgäuer, D. S.; Mayr, H. Eur. J. Org. Chem. 2014, 2014, 2956 10.1002/ejoc.201301779
47. Asahara, H.; Mayr, H. Chem.-Asian J. 2012, 7, 1401 10.1002/asia.201101046
48. Zenz, I.; Mayr, H. J. Org. Chem. 2011, 76, 9370 10.1021/jo201678u
49. Kaumanns, O.; Lucius, R.; Mayr, H. Chem.-Eur. J. 2008, 14, 9675-9682 Although these are kinetic investigations, a general method to predict the corresponding reactivities and selectivities of Michael acceptors is still missing. However, the relative reactivities of different families of Michael acceptors can be obtained by the thermodynamics of the rate-determining step, as was recently found by Mayr: H. Mayr, personal communication 10.1002/chem.200801277
50. Moraleda, D.; El Abed, D.; Pellissier, H.; Santelli, M. J. Mol. Struct.: THEOCHEM 2006, 760, 113-119 10.1016/j.theochem.2005.12.001
51. Tutkowski, B.; Meggers, E.; Wiest, O. J. Am. Chem. Soc. 2017, 139, 8062 10.1021/jacs.7b01786
52. The LUMO of the electron-deficient alkene substrate and the SOMO of the benzyl radical acting as a nucleophile are the orbitals involved in the process. The energy of the orbitals and their full structures were reported in the article.
53. Bertrand, F.; Quiclet-Sire, Z.; Zard, S. Z. Angew. Chem., Int. Ed. 1999, 38, 1943-1946 10.1002/(SICI)1521-3773(19990712)38:13/14<1943::AID-ANIE1943>3.0.CO;2-R
54. Quiclet-Sire, B.; Zard, S. Z. Beilstein J. Org. Chem. 2013, 9, 557-576 10.3762/bjoc.9.61
55. Kim, S.; Kim, S. Bull. Chem. Soc. Jpn. 2007, 80, 809-822 10.1246/bcsj.80.809
56. Chatgilialoglu, C.; Mozziconacci, O.; Tamba, M.; Bobrowski, K.; Kciuk, G.; Bertrand, M. P.; Gastaldi, S.; Timokhin, V. I. J. J. Phys. Chem. A 2012, 116, 7623-7628 10.1021/jp304863y
57. Chatgilialoglu, C. In The Chemistry of Sulfone and Sulfoxides; Patai, S.; Rapaport, Z.; Stirling, J. J. M., Eds.; Wiley, Chichester, 1988; p 1089.
58. Huang, Z.; Lu, Q.; Liu, Y.; Liu, D.; Zhang, J.; Lei, A. Org. Lett. 2016, 18, 3940-3943 10.1021/acs.orglett.6b01575
59. Chen, F.; Meng, Q.; Han, S.-Q.; Han, B. Org. Lett. 2016, 18, 3330-3333 10.1021/acs.orglett.6b01427
60. Pinnick, H. W.; Reynolds, M. A. J. Org. Chem. 1979, 44, 160 10.1021/jo01315a043
61. Chumachenko, N.; Sampson, P. Tetrahedron 2006, 62, 4540-4548 10.1016/j.tet.2006.02.043
62. Zinc Catalysis: Applications in Organic Synthesis; Enthaler, S.; Wu, X.-F., Eds.; Wiley-WCH: Weinheim, 2015.
63. The measured value of the quantum yield is similar to that found in a photoredox radical decarboxylation reaction: Miyake, Y.; Nakajima, K.; Nishibayashi, Y. Chem. Commun. 2013, 49, 7854-7856 10.1039/c3cc44438d