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Synlett 2015; 26(16): 2194-2198
DOI: 10.1055/s-0034-1381041
DOI: 10.1055/s-0034-1381041
synpacts
Domino Aryne Precursor: A Step beyond the Boundary of Traditional Aryne Chemistry
Weitere Informationen
Publikationsverlauf
Received: 22. Mai 2015
Accepted after revision: 05.06.201
Publikationsdatum:
09. Juli 2015 (online)
![](https://www.thieme-connect.de/media/synlett/201516/lookinside/thumbnails/st-2015-p0391-sp_10-1055_s-0034-1381041-1.jpg)
Abstract
In an aim to expand the scope of aryne chemistry with new synthons, a domino aryne precursor bearing an additional ortho-OTf group on Kobayashi reagent is proposed and synthesized. 2,4-Disubstituted benzothiazole could be achieved from benzothioamide derivatives and this reagent with a sequential incorporation of C–S, C–N, and C–C bonds on the consecutive positions of the aryne precursor.
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References
- 1a Wenk HH, Winkler M, Sander W. Angew. Chem. Int. Ed. 2003; 42: 502
- 1b Pellissier H, Santelli M. Tetrahedron 2003; 59: 701
- 1c Sanz R. Org. Prep. Proced. Int. 2008; 40: 215
- 1d Gampe CM, Carreira EM. Angew. Chem. Int. Ed. 2012; 51: 3766
- 1e Tadross PM, Stoltz BM. Chem. Rev. 2012; 112: 3550
-
1f Bhunia A, Yetra SR, Biju AT. Chem. Soc. Rev. 2012; 41: 3140
- 1g Dubrovskiy AV, Markina NA, Larock RC. Org. Biomol. Chem. 2013; 11: 191
- 2 Himeshima Y, Sonoda T, Kobayashi H. Chem. Lett. 1983; 1211
- 3 Sainsbury M In Aromatic Chemistry . Oxford University Press; Oxford: 1992. 1st ed.
- 4a Du C.-JF, Hart H, Ng K.-KD. J. Org. Chem. 1986; 51: 3162
- 4b Du C.-JF, Hart H. J. Org. Chem. 1987; 52: 4311
- 5a Kirkham JD, Delaney PM, Ellames GJ, Row EC, Harrity JP. A. Chem. Commun. 2010; 46: 5154
- 5b Michel B, Greaney MF. Org. Lett. 2014; 16: 2684
- 5c Rodríguez-Lojo D, Cobas A, Peña D, Pérez D, Guitián E. Org. Lett. 2012; 14: 1363
-
5d Zeng Y, Zhang L, Zhao Y, Ni C, Zhao J, Hu J. J. Am. Chem. Soc. 2013; 135: 2955
- 5e Yoshida H, Yoshida R, Takaki K. Angew. Chem. Int. Ed. 2013; 52: 8629
- 5f Hendrick CE, McDonald SL, Wang Q. Org. Lett. 2013; 15: 3444
- 5g Hall C, Henderson JL, Ernouf G, Greaney MF. Chem. Commun. 2013; 49: 7602
- 6 Medina JM, Mackey JL, Garg NK, Houk KN. J. Am. Chem. Soc. 2014; 136: 15798
- 7 Shi J, Qiu D, Wang J, Xu H, Li Y. J. Am. Chem. Soc. 2015; 137: 5670
- 8a Yoshida H, Terayama T, Ohshita J, Kunai A. Chem. Commun. 2004; 1980
- 8b Lin WW, Sapountzis I, Knochel P. Angew. Chem. Int. Ed. 2005; 44: 4258
- 8c Zhao J, Larock RC. Org. Lett. 2005; 7: 4273
- 8d Biswas K, Greaney MF. Org. Lett. 2011; 13: 4946
- 8e Pandya VG, Mhaske SB. Org. Lett. 2014; 16: 3836
- 9a Yoshida H, Shirakawa E, Honda Y, Hiyama T. Angew. Chem. Int. Ed. 2002; 41: 3247
- 9b Liu Z, Larock RC. Org. Lett. 2003; 5: 4673
- 9c Liu Z, Larock RC. J. Am. Chem. Soc. 2005; 127: 13112
- 9d Yoshida H, Morishita T, Fukushima H, Ohshita J, Kunai A. Org. Lett. 2007; 9: 3367
- 9e Okuma K, Matsunaga N, Nagahora N, Shioji K, Yokomori Y. Chem. Commun. 2011; 47: 5822
- 9f García-López J.-A, Cetin M, Greaney MF. Angew. Chem. Int. Ed. 2015; 54: 2156
- 10a Pintori DG, Greaney MF. Org. Lett. 2010; 12: 168
- 10b Fang Y, Rogness DC, Larock RC, Shi F. J. Org. Chem. 2012; 77: 6262
- 10c Saito N, Nakamura K.-i, Shibano S, Ide S, Minami M, Sato Y. Org. Lett. 2013; 15: 386