10.1002/adsc.202000657
Advanced Synthesis & Catalysis
condenser, charged with alkene (0.5 mmol) and 6 (195 mg,
0.75 mmol) was added benzene (2 mL) under N2
atmosphere. The resulting mixture was irradiated with a 300
W sun lamp (15 cm from the reaction flask) under reflux.
The disappearance of the alkene was monitored by TLC or
1H NMR (depending on the alkene used). At the end of the
reaction (typically 1–3 h), the mixture was concentrated,
and the crude product was purified by flash chromatography
on silica gel.
[16] F. Simal, A. Demonceau, A. F. Noels, Recent Res.
Dev. Org. Chem. 1999, 3, 455–464.
[17] C. Lamberth, H. Walter, F. M. Kessabi, L. Quaranta,
R. Beaudegnies, S. Trah, A. Jeanguenat, F.
Cederbaum, Phosphorus, Sulfur, Silicon Rel. Elem.
2015, 190, 1225–1235.
[18] M. Feng, B. Tang, S. H. Liang, X. Jiang, Curr. Top.
Med. Chem. 2016, 16, 1200–1216.
Acknowledgements
[19] R. J. W. Cremlyn, An Introduction to Organosulfur
Chemistry, Wiley, Chichester, 1996.
We thank the Swiss National Science Foundation (grant
200020_172621) for financial support.
[20] S. K. Patel, I. Paterson, Tetrahedron Lett. 1983, 24,
1315–1318.
References
[21] D. P. Curran, A. A. Martin-Esker, S. B. Ko, M.
[1] B. Giese, Angew. Chem. Int. Ed. Engl. 1983, 22,
753–764.
Newcomb, J. Org. Chem. 1993, 58, 4691–4695.
[22] B. Quiclet-Sire, S. Z. Zard, Chimia 2012, 66, 404–
[2] B. Giese, Radicals in Organic Synthesisꢀ: Formation
of Carbon-Carbon Bonds, Pergamon Press, Oxford,
New York, 1986.
412.
[23] S. W. McCombie, B. Quiclet-Sire, S. Z. Zard,
Tetrahedron 2018, 74, 4969–4979.
[3] P. Renaud, M. P. Sibi, Radicals in Organic
Synthesis, Wiley, Weinheim, 2001.
[24] S. Z. Zard, Helv. Chim. Acta 2019, 102, e1900134.
[25] D. H. R. Barton, S. Z. Zard, Janssen Chim. Acta
1986, 4, 3–9.
[4] C. Chatgilialoglu, A. Studer, Encyclopedia of
Radicals in Chemistry, Biology and Materials,
Wiley, Chichester, 2012.
[26] M. F. Saraiva, M. R. C. Couri, M. Le Hyaric, M. V.
de Almeida, Tetrahedron 2009, 65, 3563–3572.
[5] J. Byers, in Radicals in Organic Synthesis (Eds.:
M.P. Sibi, P. Renaud), Wiley, 2008, pp. 72–89.
[27] A.-P. Schaffner, F. Montermini, D. Pozzi, V.
Darmency, E. M. Scanlan, P. Renaud, Adv. Synth.
Catal. 2008, 350, 1163–1167.
[6] D. P. Curran, NATO ASI Ser., Ser. C 1989, 260, 37–
51.
[28] S. Kim, S. Kim, Bull. Chem. Soc. Jpn. 2007, 80,
809–822.
[7] D. P. Curran, M. H. Chen, E. Spletzer, C. M. Seong,
C. T. Chang, J. Am. Chem. Soc. 1989, 111, 8872–
8878.
[29] F. Bertrand, F. Le Guyader, L. Liguori, G. Ouvry, B.
Quiclet-Sire, S. Seguin, S. Z. Zard, C. R. Acad. Sci.,
Ser. IIc: Chim. 2001, 4, 547–555.
[8] D. P. Curran, E. Bosch, J. Kaplan, M. Newcomb, J.
Org. Chem. 1989, 54, 1826.
[30] T. Billard, N. Roques, B. R. Langlois, Tetrahedron
Lett. 2000, 41, 3069–3072.
[9] K. Weidner, A. Giroult, P. Panchaud, P. Renaud, J.
Am. Chem. Soc. 2010, 132, 17511–17515.
[31] S. Kim, K.-C. Lim, S. Kim, Chem. Commun. 2007,
4507–4509.
[10] L. Cao, K. Weidner, P. Renaud, Adv. Synth. Cat.
2011, 353, 3467–3472.
[32] T. Billard, B. R. Langlois, S. Large, D. Anker, N.
Roidot, P. Roure, J. Org. Chem. 1996, 61, 7545–
7550.
[11] L. Cao, C. Jimeno, K. Weidner, P. Renaud, Adv.
Synth. Cat. 2012, 354, 2070–2070.
[12] P. Renaud, C. Ollivier, P. Panchaud, P. Panchaud,
[33] S. Cren, P. Schär, P. Renaud, K. Schenk, J. Org.
Chem. 2009, 74, 2942–2946.
Angew. Chem. Int. Ed. 2002, 41, 3460–3462.
[13] P. Panchaud, P. Renaud, J. Org. Chem. 2004, 69,
3205–3207.
[34] L. Field, J. Am. Chem. Soc. 1952, 74, 394–398.
[35] S. A. Wolckenhauer, A. S. Devlin, J. Du Bois, Org.
Lett. 2007, 9, 4363–4366.
[14] W. T. Eckenhoff, T. Pintauer, Catal. Rev.: Sci. Eng.
2010, 52, 1–59.
[36] V. N. Sergeev, A. G. Shipov, G. S. Zaitseva, Yu. I.
[15] T. Pintauer, Eur. J. Inorg. Chem. 2010, 2449–2460.
Baukov, Zh. Obshch. Khim. 1979, 49, 2753.
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