ACS Catalysis
Letter
(2) Aromatic sulfenylations and hydrosulfenylations (a) Iron: (i)
Correa, A.; Carril, M.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47,
2880−2883. (ii) Wu, J.-R.; Lin, C.-H.; Lee, C.-F. Chem. Commun.
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Lin, H.-P.; Lee, C.-F. Chem. Commun. 2010, 46, 282−284. (c)
Palladium: Fernandez-Rodríguez, M. A.; Shen, Q.; Hartwig, J. F. J.
́
Am. Chem. Soc. 2006, 128, 2180−2181.
(3) Allylic sulfenylations and hydrosulfenylations: (a) Iridium:
Zheng, S.; Gao, N.; Liu, W.; Liu, D.; Zhao, X.; Cohen, T. Org. Lett.
2010, 12, 4454. (b) Palladium: (i) Goux, C.; Lohste, P.; Sinou, D.
Tetrahedron Lett. 1992, 33, 8099. (ii) Goux, C.; Lohste, P.; Sinou, D.
Tetrahedron Lett. 1994, 34, 10321.
(iii) Frank, M.; Gais, H.-J.
Tetrahedron: Asymmetry 1998, 9, 3353. (iv) (i) Gais, H.-J.; Jagusch, T.;
Spalthoff, N.; Gerhards, F.; Frank, M.; Raabe, G. Chem.Eur. J. 2003,
9, 4202. (c) Ruthenium: Zaitsev, A. B.; Caldwell, H. F.; Pregosin, P.
S.; Veiros, L. F. Chem.Eur. J. 2009, 15, 6468. (d) Iron: Lin, Y.-Y.;
Wang, Y.-J.; Lin, C.-H.; Cheng, J.-H.; Lee, C.-F. J. Org. Chem. 2012, 77,
6100−6106. (e) Gao, N.; Zheng, S.; Yang, W.; Zhao, X. Org. Lett.
2011, 13, 1514. (f) A review is found in Liu, W.; Zhao, Y. Synthesis
2013, 2051.
(4) Reviews: (a) C,S bond formation in biological systems:
Fontecave, M.; Ollagnier-De-Choudens, S.; Mulliez, E. Chem. Rev.
2003, 103, 2149. (b) “Click”-type chemistry using thiols: Hoyle, C.
E.; Lowe, A. B.; Bowman, C. N. Chem. Soc. Rev. 2010, 39, 1355. (c)
Science of Synthesis: Category 5, Compounds with One Saturated Carbon
Heteroatom Bond. Sulfur, Selenium, and Tellurium; Kambe, N., Aleman,
J., Eds.; Thieme-Verlag: Stuttgart, Germany, 2008. (d) Metal-
catalyzed C,S bond formations: Kondo, T.; Mitsudo, T. Chem. Rev.
2000, 100, 3205.
(5) (a) Copper: Garg, S. K.; Kumar, R.; Chakraborti, A. K.
Tetrahedron Lett. 2005, 46, 1721−1724. (b) Nickel: Kanemasa, S.;
Oderaotoshi, Y.; Wada, E. J. Am. Chem. Soc. 1999, 121, 8675−8676.
(c) For a review on sulfa-Michael additions, see: Enders, D.; Luttgen,
̈
K.; Narine, A. A. Synthesis 2007, 959 see also refs 2 and 3.
(6) Delp, S. A.; Munro-Leighton, C.; Goj, L. A.; Ramírez, M. A.;
Gunnoe, T. B.; Petersen, J. L.; Boyle, P. D. Inorg. Chem. 2007, 46,
2365−2367.
(7) (a) Hsieh, C.-H.; Darensbourg, M. Y. J. Am. Chem. Soc. 2010,
132, 14118−14125. (b) Pulukkody, R.; Kyran, S. J.; Bethel, R. D.;
Hsieh, C.-H.; Hall, M. B.; Darensbourg, D. J.; Darensbourg, M. Y. J.
Am. Chem. Soc. 2013, 135, 8423−8430.
(8) Holzwarth, M. S.; Frey, W.; Plietker, B. Chem. Commun. 2011, 47,
11113−11115.
(9) For monographs on iron catalysis, see: (a) Iron Catalysis:
Fundamentals and Applications: 33 (Topics in Organometallic
Chemistry); Plietker, B., Ed.; Springer: Berlin, 2010, Vol. 1. (b) Iron
Catalysis in Organic Chemistry: Reactions and Applications; Plietker, B.,
Ed.; Wiley-VCH: Weinheim, 2008, Vol. 1. For selected reviews on
iron catalysis,see: (c) Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem.
Rev. 2004, 104, 6217−6254. (d) Correa, A.; Mancheno, O. G.; Bolm,
C. Chem. Soc. Rev. 2008, 37, 1108−1117. (e) Czaplik, W. M.; Mayer,
M.; Cvengros, J.; Jacobi von Wangelin, A. ChemSusChem 2009, 38,
396−417. (f) Morris, R. H. Chem. Soc. Rev. 2009, 38, 2282−2291.
(g) Darwish, M.; Wills, M. Catal. Sci. Technol. 2012, 2, 243−255. For
an account,see: (h) Sherry, B. D.; Furstner, A. Acc. Chem. Res. 2008,
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41, 1500−1511.
(10) Yamada, H.; Kinoshita, H.; Inomata, K.; Kotake, H. Bull. Chem.
Soc. Jpn. 1983, 56, 949−950.
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dx.doi.org/10.1021/cs4009336 | ACS Catal. 2013, 3, 3002−3005