10.1002/chem.201604567
Chemistry - A European Journal
Kajitani, E. Nishinaka, M. Sonoda, A. Ogawa, J. Sulfur Chem. 2009, 30,
309–318; e) V. P. Ananikov, N. V. Orlov, I. P. Beletskaya, V. Khrustalev,
M. Y. Antipin, T. V. Timofeeva, J. Am. Chem. Soc. 2007, 129, 7252–
7253; f) A. Kondoh, H. Yorimitsu, K. Oshima, Org. Lett. 2007, 9, 1383–
1385; g) B. Gabriele, G. Salerno, A. Fazio, Org. Lett. 2000, 2, 351–352.
h) J.-E. Bäckvall, A. Ericsson, J. Org. Chem. 1994, 59, 5850–5851; i) H.
Kuniyasu, A. Ogawa, K.-I Sato, I. Ryu, N. Kambe, N. Sonoda, J. Am.
Chem. Soc. 1992, 114, 5902–5903.
support from the Spanish MINECO-FEDER (CTQ2014-51999-P
to E.P. and CTQ2013-44303-P and CTQ2014-51912-REDC to
I.F.), UJI (P11B2014-02 to E.P.). D.I.B and I.S. gratefully
acknowledge the National Research Foundation, South Africa
(NRF 87890, 103698 and 92521), and Sasol Technology R&D
Pty. Ltd., South Africa for financial support.
[7]
a) V. P. Ananikov, N. V. Gayduck, N. V. Orlov, I. P. Beletskaya, V. N.
Khrustalev, M. Y. Antipin, Chem. Eur. J. 2010, 16, 2063–2071; b) D. A.
Malyshev, N. M. Scott, N. Marion, E. D. Stevens, V. P. Ananikov, I. P.
Beletskaya, S. P. Nolan, Organometallics 2006, 25, 4462–4470; c) V. P.
Ananikov, L. P. Orlov, I. P. Beletskaya, Organometallics 2006, 25,
1970–1977; d) V. P. Ananikov, D. A. Malyshev, I. P. Beletskaya, G. G.
Aleksandrov, I. L. Eremenko, Adv. Synth. Catal. 2005, 347, 1993–2001;
e) L. -B. Han, C. Zhang, H. Yazawa, S. Shimada, J. Am. Chem. Soc.
2004, 126, 5080–5081.
Keywords: rhodium(I) • hydrothiolation • 1,2,3-triazol-5-ylidene
(TRZ) • mesoionic carbene (MIC) • hemilabile
[1]
For selected examples of vinyl sulfides with biological applications, see:
a) C. A. Dvorak, W. D. Schmitz, D. J. Poon, D. C. Pryde, J. P. Lawson,
R. A. Amos, A. I. Meyers, Angew. Chem., Int. Ed. 2000, 39, 1664–
1666; b) M. Ceruti, G. Balliano, F. Rocco, P. Milla, S. Arpicco, L. Cattel,
F. Viola, Lipids 2001, 36, 629–636; c) P. Johannesson, G. Lindeberg, A.
Johansson, G. V. Nikiforovich, A. Gogoll, B. Synnergren, M. LeGrèves,
F. Nyberg, A. Karlén, A. Hallberg, J. Med. Chem. 2002, 45, 1767–1777;
d) Á. Szilágyi, F. Fenyvesi, O. Majercsik, I. F. Pelyvás, I. Bácskay, P.
Fehér, J. Váradi, M. Vecsernyés, P. Herczegh, J. Med. Chem. 2006, 49,
5626–5630; e) M. C. Aversa, A. Baratucci, P. Bonaccorsi, F. Marino-
Merlo, A. Mastino, M. T. Sciortino, Bioorg. Med. Chem. 2007, 17, 1456–
1463.
[8]
[9]
D. I. Bezuidenhout, G. Kleinhans, G. Guisado-Barrios, D. C. Liles, G.
Ung, G. Bertrand, Chem.Commun. 2014, 50, 2431–2433.
For recent reviews, see: a) R. H. Morris, Acc. Chem. Res. 2015, 48,
1494–1502; b) J. R. Khusnutdinova, D. Milstein, D. Angew. Chem.
2015, 127, 12406–12445; Angew. Chem. Int. Ed. 2015, 54, 12236–
12273; c) T. Zell, D. Milstein, Acc. Chem. Res. 2015, 48, 1979–1994; d)
S. Kuwata, T. Ikariya, Chem. Commun. 2014, 50, 14290–14300; e) D.
Gelman, M. Sanaa, ACS Catal. 2012, 2, 2456–2466. f) B. Askevold, H.
W. Roesky, S. Schneider, ChemCatChem. 2012, 4, 307–320; g) W.
Kaim, Eur. J. Inorg. Chem. 2012, 343–348; h) W. I. Dzik, B. de Bruin,
Organometallic Chemistry 2011, 37, 47–78; i) C. Gunanathan, D.
Milstein, Acc. Chem. Res. 2011, 44, 588–602; j) H. Grützmacher,
Angew. Chem. 2008, 120, 1838–1842; Angew. Chem. Int. Ed. 2008,
47, 1814–1818.
[2]
For selected examples of vinyl sulfides as polymers, see: a) J. Liu, J.
W. Y. Lam, C. K. Jim, J. C. Y. Ng, J. Shi, H. Su, K. F. Yeung, Y. Hong,
M. Faisel, Y. Yu, K.S. Wong, B. Z. Tang, Macromolecules 2011, 44,
68–79; b) A. B. Lowe, J. W. Chan, in Functional Polymers by Post-
Polymerization Modification; P. Theato, H.-A. Eds. Klok, Wiley-VCH
Verlag GmbH & Co. KGaA: Weinheim, 2013, pp. 87–118; c) B. Yao, J.
Mei, J. Li, J. Wang, H. Wu, J. Z. Sun, A. Qin, B. Z. Tang,
Macromolecules 2014, 47, 1325–1333; d) I. -T. Trotuş, T. Zimmermann,
F. Schüth, Chem. Rev. 2014, 114, 1761–1782.
[10] a) R. Lalrempuia, N. D. McDaniel, H. Müller-Bunz, S. Bernhard, M.
Albrecht, Angew. Chem. Int. Ed. 2010, 122, 9959–9962; Angew. Chem.
2010, 49, 9765–9768; b) Cao, R.; Lai, W.; Du, P. Energy Environ. Sci.
2012, 5, 8134–8157; c) D. Canseco-Gonzalez, A. Petronilho, H.
Mueller-Bunz, K. Ohmatsu, T. Ooi, M. Albrecht, J. Am. Chem. Soc.
2013, 135, 13193–13203.
[3]
[4]
For recent reviews, see: a) J. A. Love, M. Wathier, Eur. J. Inorg. Chem.
2016, 23911–2402; b) A. Dondoni, A. Marra, Eur. J. Org. Chem. 2014,
3955–39659; c) R. Chinchilla, C. Nájera, Chem. Rev. 2014, 114, 1783–
1826; d) R. Castarlenas, A. Di Giuseppe, J. J. Pérez-Torrente, L. A.
Oro, Angew. Chem. 2013, 125, 223 –234; Angew. Chem. Int. Ed. 2013,
52, 211–222; (e) I. P. Beletskaya, V. P. Ananikov, Chem. Rev. 2011,
111–1636.
[11] The synthesis, spectroscopic characterization and single crystal X-ray
structures of the new triazolium salts A–C are reported in the
Supporting Information.
a) G. Kleinhans, G. Guisado-Barrios, D. C. Liles, G. Bertrand, D. I.
Bezuidenhout, Chem. Commun. 2016, 52, 3504–3507; b) S. Kankala, S.
Nerella, R. Vadde, C. S. Vassam, RSC Adv. 2013, 3, 23582–23588; c)
L. Palacios, M. J. Artigas, V. Polo, F. J. Lahoz, R. Castarlenas, J. J.
Pérez-Torrente, L. A. Oro, L. A. ACS Catal. 2013, 3, 2910–2919; d) A.
Di Giuseppe, R. Castarlenas, J. J. Pérez-Torrente, M. Crucianelli, R.
Sancho, F. J. Lahoz, L. A. Oro, J. Am. Chem. Soc. 2012, 134, 8171–
8183; e) J. Yang, A. Sabarre, L. R. Fraser, B. O. Patrick, J. A. Love, J.
Org. Chem. 2009, 74, 182–187; f) L. R. Fraser, J. Bird, Q. Wu, C. Cao,
B. O. Patrick, J. A. Love, J. A. Organometallics 2007, 26, 5602–5611;
g) Y. Misumi, H. Seino, Y. Mizobe, J. Organomet. Chem. 2006, 691,
3157–3164; h) C. Cao, L.R Fraser, J. A. Love, J. Am. Chem. Soc.
2005, 127, 17614–17615.
[12] J. Bouffard, B. K. Keitz, R. Tonner, G. Guisado-Barrios, G. Frenking, R.
H. Grubbs, G. Bertrand, Organometallics 2011, 30, 2617–2627.
[13] G. Guisado-Barrios, J. Bouffard, B. Donnadieu, G. Bertrand, Angew.
Chem. Int. Ed. 2010, 122, 4869–4872; Angew. Chem. 2010, 49, 4759–
4762.
[14] a) D. Mendoza-Espinosa, R. González-Olvera, G. E. Negrón-Silva, D.
Angeles-Beltrán, O. R. Suárez-Castillo, A. Álvarez-Hernández, R.
Santillan, Organometallics 2015, 34, 4529–4542; b) T. V. Q. Nguyen,
W.-J. Yoo, S. Kobayashi, Angew. Chem. 2015, 127, 9341–9344;
Angew. Chem. Int. Ed. 2015, 54, 9209–9212; c) X. Yan, J. Bouffard, G.
Guisado-Barrios, B. Donnadieu, G. Bertrand, Chem. Eur. J. 2012, 18,
14627–14631; d) M. T. Zamora, M. J. Ferguson, M. Cowie,
Organometallics 2012, 31, 5384–5395; e) A. Poulain, D. Canseco-
Gonzalez, R. Hynes-Roche, H. Müller-Bunz, O. Schuster, H. Stoeckli-
Evans, A. Neels, M. Albrecht, Organometallics 2011, 30, 1021–1029; f)
P. Mathew, A. Neels, M. Albrecht, J. Am. Chem. Soc. 2008, 130.
13534–13535.
[5]
a) H. Zhao, J. Peng, M. Cai, M. Catal. Lett. 2012, 142, 138–142; b) L. D.
Field, B. A. Messerle, K. Q. Vuong, P. Turner, Dalton Trans. 2009,
3599–3614; c) S. Shoai, P. Bichler, B. Kang, H, Buckley, J. A. Love,
Organometallics 2007, 26, 5778–5781; d) S. Burling, L. D. Field B. A
Messerle, K. Q. Vuong, P. Turner, Dalton Trans. 2003, 4181–4191; e)
A. Ogawa, T. Ikeda, K. Kimura, J. Hirao, J. Am. Chem. Soc. 1999, 121,
5108–5114.
[15] a) D. R. Anton, R. H. Crabtree, Organometallics 1983, 2, 855−859; b) J.
A. Widegren, R. G. Finke, J. Mol. Catal. A 2003, 198, 317−341.
[16] a) W. Wylie, A. J. Lough, R. H. Morris, Organometallics 2011, 30, 1236-
1252; b) W. Wylie, A. J. Lough, R. H. Morris, Organometallics 2012, 31,
2152–2165.
[6] a) R. Gerber, C. M. Frech, Chem. Eur. J. 2012, 18, 8901–8905; b) V. P.
Ananikov, N. V. Orlov, S. S. Zalesskiy, I. P. Beletskaya, V. N.
Khrustalev, K. Morokuma, D. G. Musaev, J. Am. Chem. Soc. 2012, 134,
6637–6649; c) T. Mitamura, M. Daitou, A. Nomoto, A. Ogawa, A. Bull.
Chem. Soc. Jpn. 2011, 84, 413–415; d) S. Kodama, A. Nomoto, A.; M.
[17] An alternative reaction mechanism involving a related INT3 having a
square pyramidal Rh(I) cannot be discarded. For related species, see:
a) L. D. Field, B. A. Messerle, K. Q. Vuong, P. Turner, Organometallics
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