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Synlett 2013; 24(5): 587-590
DOI: 10.1055/s-0032-1318271
DOI: 10.1055/s-0032-1318271
letter
Z-Selective Dimerization of Aromatic Terminal Alkynes Catalyzed by an Iridium(I)–N-Heterocyclic Carbene–Phosphine System
Further Information
Publication History
Received: 10 January 2013
Accepted after revision: 30 January 2013
Publication Date:
18 February 2013 (online)
Abstract
The development of an iridium-catalyzed regio- and stereoselective dimerization process has enabled the formation of (Z)-enyne products. More specifically, low catalyst loadings of an iridium(I) complex, featuring a bulky N-heterocyclic carbene–phosphine ligand combination, has been successfully employed in this selective head-to-head dimerization of terminal alkynes via C–H activation.
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References and Notes
- 1 Trost BM. Angew. Chem., Int. Ed. Engl. 1995; 34: 259
- 2 Nicolaou KC, Dai WM, Tsay SC, Estevez VA, Wrasidlo W. Science 1992; 256: 1172
- 3 Liu Y, Nishiura M, Wang Y, Hou Z. J. Am. Chem. Soc. 2006; 128: 5592
- 4 Zhang L, Sun S, Kroll J, Luo Y. Synlett 2012; 23: 54
- 5a Trost BM, Sorum MT, Chan C, Harms AE, Ruhter G. J. Am. Chem. Soc. 1997; 119: 698
- 5b Lucking U, Pfaltz A. Synlett 2000; 1261
- 6 Midya GC, Paladhi S, Dhara K, Dash J. Chem. Commun. 2011; 47: 6698
- 7 Ogoshi S, Ueta M, Oka MA, Kurosawa H. Chem. Commun. 2004; 2732
- 8a Jun C, Zheng L, Crabtree RH. Tetrahedron Lett. 1992; 33: 7119
- 8b Ogata K, Toyota A. J. Organomet. Chem. 2007; 692: 4139
- 8c Ohmura T, Yorozuya SI, Yamamoto Y, Miyaura N. Organometallics 2000; 19: 365
- 8d Ogata K, Oka O, Toyota A, Suzuki N, Fukuzawa SI. Synlett 2008; 2663
- 9 Platel RH, Schafer LL. Chem. Commun. 2012; 48: 10609
- 10 Gevorgyan V, Rubin M, Sromek AW. Synlett 2003; 2265
- 11a Wakatsuki Y, Yamazaki H, Kumegawa N, Satoh T, Satoh JY. J. Am. Chem. Soc. 1991; 113: 9604
- 11b Yi CS, Liu N. Organometallics 1996; 15: 3968
- 12a Katagiri T, Tsurugi H, Satoh T, Miura M. Chem. Commun. 2008; 3405
- 12b Melis K, De Vos D, Jacobs P, Verpoort F. J. Organomet. Chem. 2002; 659: 159
- 13 Nishiura M, Hou Z, Wakatsuki Y, Yamaki T, Miyamoto T. J. Am. Chem. Soc. 2003; 125: 1184
- 14a Brown JA, Irvine S, Kennedy AR, Kerr WJ, Andersson S, Nilsson GN. Chem. Commun. 2008; 1115
- 14b Nilsson GN, Kerr WJ. J. Labelled Compd. Radiopharm. 2010; 53: 662
- 14c Complexes 1a–c are available commercially from Strem Chemicals.
- 15a Crabtree RH, Felkin H, Morris GE. J. Organomet. Chem. 1977; 141: 205
- 15b Crabtree RH. Acc. Chem. Res. 1979; 12: 331
- 15c Hesk D, Das PR, Evans B. J. Labelled Compd. Radiopharm. 1995; 36: 497
- 15d Ellames GJ, Gibson JS, Herbert JM, McNeill AH. Tetrahedron 2001; 57: 9487
- 16 Bennie LS, Fraser CJ, Irvine S, Kerr WJ, Andersson S, Nilsson GN. Chem. Commun. 2011; 47: 11653
- 17a Schäfer M, Mahr N, Wolf J, Werner H. Angew. Chem., Int. Ed. Engl. 1993; 32: 1315
- 17b Wakatsuki Y, Yamazaki H, Kumegawa N, Johar PS. Bull. Chem. Soc. Jpn. 1993; 66: 987
- 18a Webster CE, Hall MB. Coord. Chem. Rev. 2003; 238-239: 315
- 18b Kawamura K, Hartwig JF. J. Am. Chem. Soc. 2001; 123: 8422
- 18c Meredith JM, Robinson RJr, Goldberg KI, Kaminsky W, Heinekey DM. Organometallics 2012; 31: 1879
- 20 Kuang C, Yang Q, Senboku H, Tokuda M. Tetrahedron 2005; 61: 4043
- 21 Galli C, Gentili P, Rapport Z. J. Org. Chem. 1994; 59: 6786