Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2015; 47(17): 2670-2676
DOI: 10.1055/s-0034-1380755
DOI: 10.1055/s-0034-1380755
paper
One-Pot Synthesis of 1-Alkenyl Sulfides from Alkynes and Organic Disulfides with the Use of Organoaluminums
Further Information
Publication History
Received: 27 February 2015
Accepted after revision: 16 April 2015
Publication Date:
19 June 2015 (online)
Abstract
Organic disulfides (dipropyl, dihexyl, or diphenyl disulfide) are convenient and efficient agents for the sulfanylation of 1-alkenylaluminum derivatives.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380755.
- Supporting Information
-
References
- 1 Zyk NV, Beloglazkina EK, Belova MA, Dubinina NS. Russ. Chem. Rev. 2003; 72: 769
- 2 Kondo T, Mitsudo T.-a. Chem. Rev. 2000; 100: 3205
- 3 Palani T, Park K, Song KH, Lee S. Adv. Synth. Catal. 2013; 355: 1160
- 4 Downey CW, Craciun S, Neferu AM, Vivelo CA, Mueller CJ, Southall BC, Corsi S, Etchill EW, Sault RJ. Tetrahedron Lett. 2012; 53: 5763
- 5 Shoai S, Bichler P, Kang B, Buckley H, Love JA. Organometallics 2007; 26: 5778
- 6 Yang Y, Rioux RM. Chem. Commun. 2011; 47: 6557
- 7 Corma A, González-Arellano C, Iglesias M, Sánchez F. Appl. Catal., A. 2010; 375: 49
- 8 Weiss CJ, Wobser SD, Marks TJ. Organometallics 2010; 29: 6308
- 9 Cao C, Fraser LR, Love JA. J. Am. Chem. Soc. 2005; 127: 17614
- 10 Weiss CJ, Marks TJ. J. Am. Chem. Soc. 2010; 132: 10533
- 11 Malyshev DA, Scott NM, Marion N, Stevens ED, Ananikov VP, Beletskaya IP, Nolan SP. Organometallics 2006; 25: 4462
- 12 Bates CG, Saejueng P, Doherty MQ, Venkataraman D. Org. Lett. 2004; 6: 5005
- 13 Lin Y.-Y, Wang Y.-J, Lin C.-H, Cheng J.-H, Lee C.-F. J. Org. Chem. 2012; 77: 6100
- 14 Reddy VP, Swapna K, Kumar AV, Rao KR. Tetrahedron Lett. 2010; 51: 293
- 15 Ranu BC, Dey R, Chatterjee T, Ahammed S. ChemSusChem 2012; 5: 22
- 16 Ogawa T, Hayami K, Suzuki H. Chem. Lett. 1989; 18: 769
- 17 Wang Z.-L, Tang R.-Y, Luo P.-S, Deng C.-L, Zhong P, Li J.-H. Tetrahedron 2008; 64: 10670
- 18 Neumann H, Seebach D. Tetrahedron Lett. 1976; 17: 4839
- 19 Van Horn DE, Negishi E. J. Am. Chem. Soc. 1978; 100: 2252
- 20 Negishi E, Van Horn DE, Yoshida T. J. Am. Chem. Soc. 1985; 107: 6639
- 21 Van Horn DE, Negishi E. J. Am. Chem. Soc. 1978; 100: 2252
- 22 Zakharkin LI, Gavrilenko VV. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1960; 9: 1294
- 23 Ibragimov AG, Ramazanov IR, Khalilov LM, Sultanov RM, Dzhemilev UM. Mendeleev Commun. 1996; 6: 231
- 24 Dzhemilev UM, Ibragimov AG, Zolotarev AP. Mendeleev Commun. 1992; 2: 135
- 25 Dzhemilev UM, Ibragimov AG, Zolotarev AP, Muslukhov RR, Tolstikov GA. Bull. Acad. Sci. USSR. Div. Chem. Sci. (Engl. Transl.) 1989; 38: 194
- 26 Patnode WI, Schmidt FC. J. Am. Chem. Soc. 1945; 67: 2272
- 27 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA. J, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam NJ, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, Revision A.1. Gaussian, Inc; Wallingford: 2009
- 28 Ager DJ. J. Chem. Soc., Perkin Trans. 1 1986; 183