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Synthesis 2013; 45(5): 609-614
DOI: 10.1055/s-0032-1316855
DOI: 10.1055/s-0032-1316855
paper
Iron(III)-Catalyzed Dehydration C(sp2)–C(sp2) Coupling of Tertiary Propargyl Alcohols and α-Oxo Ketene Dithioacetals: A New Route to gem-Bis(alkylthio)-Substituted Vinylallenes
Further Information
Publication History
Received: 09 January 2013
Accepted after revision: 23 January 2013
Publication Date:
06 February 2013 (online)
![](https://www.thieme-connect.de/media/synthesis/201305/lookinside/thumbnails/10.1055-s-0032-1316855-1.jpg)
Abstract
A new and efficient synthetic approach to [gem-bis(alkylthio)vinyl]allenes has been developed involving iron(III)-catalyzed dehydration C(sp2)–C(sp2) coupling of tertiary propargyl alcohols and α-oxo ketene dithioacetals, affording a variety of [gem-bis(alkylthio)vinyl]allenes in good to excellent yields.
Key words
iron catalysis - tertiary propargyl alcohols - α-oxo ketene dithioacetals - allenic carbocation - [gem-bis(alkylthio)vinyl]allenesSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1a Robinson JM, Sakai T, Okano K, Kitawaki T, Danheiser RL. J. Am. Chem. Soc. 2010; 132: 11039
- 1b Regás D, Ruiz JM, Afonso MM, Palenzuela JA. J. Org. Chem. 2006; 71: 9153
- 1c Ruiz JM, Regás D, Afonso MM, Palenzuela JA. J. Org. Chem. 2008; 73: 7246
- 2a Souto JA, López CS, Faza ON, Alvarez R, de Lera AR. Org. Lett. 2005; 7: 1565
- 2b Murakami M, Itami K, Ito Y. Angew. Chem., Int. Ed. Engl. 1995; 34: 2691
- 3 Delas C, Urabe H, Sato F. J. Am. Chem. Soc. 2001; 123: 7937
- 4a Faza ON, López CS, de Lera AR. J. Org. Chem. 2007; 72: 2617
- 4b Knudsen CG, Carey SC, Okamura WH. J. Am. Chem. Soc. 1980; 102: 6355
- 5a Wu Y, West FG. J. Org. Chem. 2010; 75: 5410
- 5b Funami H, Kusama H, Iwasawa N. Angew. Chem. Int. Ed. 2007; 46: 909
- 5c Lee JH, Toste FD. Angew. Chem. Int. Ed. 2007; 46: 912
- 5d Cergol KM, Newton CG, Lawrence AL, Willis AC, Paddon-Row MN, Sherburn MS. Angew. Chem. Int. Ed. 2011; 50: 10425
- 6a Krause N, Purpura M. Angew. Chem. Int. Ed. 2000; 39: 4355
- 6b Purpura M, Krause N. Eur. J. Org. Chem. 1999; 267
- 6c Dulcere J.-P, Grimaldi J, Santelli M. Tetrahedron Lett. 1981; 22: 3179
- 6d Dulcere JP, Roumestant ML, Gore J. Tetrahedron Lett. 1972; 13: 4465
- 7a Murakami M, Amii H, Itami K, Ito Y. Angew. Chem., Int. Ed. Engl. 1995; 34: 1476
- 7b Murakami M, Ashida S, Matsuda T. J. Am. Chem. Soc. 2004; 126: 10838
- 8 For a recent review on the chemistry of ketene dithioacetals, see: Pan L, Bi X, Liu Q. Chem. Soc. Rev. 2013; 42: 1251
- 9a Modern Allene Chemistry . Krause N, Hashmi AS. K. Wiley-VCH; Weinheim: 2004
-
9b Ma S. Chem. Rev. 2005; 105: 2829
- 9c Sydnes LK. Chem. Rev. 2003; 103: 1133
- 10 Fang Z, Yuan H, Liu Y, Tong Z, Li H, Yang J, Barry B, Liu J, Liao P, Zhang J, Liu Q, Bi X. Chem. Commun. 2012; 48: 8802
- 11 Song J, Fang Z, Liu Y, Li R, Xu L, Barry B, Liu Q, Bi X. Synlett 2011; 2551
- 12 Yoshida M, Gotou T, Ihara M. Tetrahedron Lett. 2004; 45: 5573
- 13a Swaminathan S, Narayanan KV. Chem. Rev. 1971; 71: 429
- 13b Edens M, Boerner D, Chase CR, Nass D, Schiavelli MD. J. Org. Chem. 1977; 42: 3403
- 14a Wang S, Zhu Y, Wang Y, Lu P. Org. Lett. 2009; 11: 2615
- 14b Zhu Y, Yin G, Hong D, Lu P, Wang Y. Org. Lett. 2011; 13: 1024
- 14c Yin G, Zhu Y, Lu P, Wang Y. J. Org. Chem. 2011; 76: 8922
- 14d Zhu Y, Wen S, Yin G, Hong D, Lu P, Wang Y. Org. Lett. 2011; 13: 3553
- 14e Yin G, Zhu Y, Zhang L, Lu P, Wang Y. Org. Lett. 2011; 13: 940
- 14f Chen X, Wang H, Jin X, Feng J, Wang Y, Lu P. Chem. Commun. 2011; 47: 2628
- 14g Zhang L, Zhu Y, Yin G, Lu P, Wang Y. J. Org. Chem. 2012; 77: 9510
- 15a Zhang X, Teo WT, Chan PW. H. Org. Lett. 2009; 11: 4990
- 15b Zhang X, Teo WT, Chan PW. H. J. Org. Chem. 2010; 75: 6290
- 15c Rao W, Chan PW. H. Org. Biomol. Chem. 2010; 8: 4016
- 15d Kothandaraman P, Mothe SR, Toh SS. M, Chan PW. H. J. Org. Chem. 2011; 76: 7633
- 15e Mothe SR, Lauw SJ. L, Kothandaraman P, Chan PW. H. J. Org. Chem. 2012; 77: 6937
- 15f Susanti D, Koh F, Kusuma JA, Kothandaraman P, Chan PW. H. J. Org. Chem. 2012; 77: 7166
- 16a Yao L.-F, Tan D, Miao X, Huang K.-W. RSC Adv. 2012; 2: 7594
- 16b Guo L.-N, Duan X.-H, Liang Y.-M. Acc. Chem. Res. 2011; 44: 111
- 16c Zhu H.-T, Ji K.-G, Yang F, Wang L.-J, Zhao S.-C, Ali S, Liu X.-Y, Liang Y.-M. Org. Lett. 2011; 13: 684
- 16d Wang T, Chen X, Chen L, Zhan Z. Org. Lett. 2011; 13: 3324
- 16e Pan Y, Zhao S, Ji W, Zhan Z. J. Comb. Chem. 2009; 11: 103
- 17a Wang Y, Li W, Che G, Bi X, Liao P, Zhang Q, Liu Q. Chem. Commun. 2010; 46: 6843
- 17b Wang Y, Bi X, Li D, Liao P, Wang Y, Yang J, Zhang Q, Liu Q. Chem. Commun. 2011; 47: 809
- 17c Xiong T, Li Y, Bi X, Lv Y, Zhang Q. Angew. Chem. Int. Ed. 2011; 50: 7140
- 17d Wang Y, Bi X, Li W, Li D, Zhang Q, Liu Q, Ondon BS. Org. Lett. 2011; 13: 1722
- 17e Hu Y, Fu X, Barry B.-D, Bi X, Dong D. Chem. Commun. 2012; 48: 690
- 17f Wang Z, Bi X, Liao P, Zhang R, Liang Y, Dong D. Chem. Commun. 2012; 48: 7076
- 17g Xiang D, Bi X, Liao P, Fang G, Wang Z, Xin X, Dong D. RSC Adv. 2013; 3: 386
- 17h Wang Z, Bi X, Liao P, Lin X, Dong D. Chem. Commun. 2013; 49: 1309
- 18 For reviews on the iron-catalyzed organic reactions, see: Iron Catalysis in Organic Chemistry: Reactions and Applications. Plietker B. Wiley-VCH; Weinheim: 2008
For examples of the substituent-regulated reactivity of vinylallenes, see:
For selected reviews of allenes, see: