RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2023; 55(05): 779-785
DOI: 10.1055/a-1953-4534
DOI: 10.1055/a-1953-4534
paper
Disilathiane as a Sulfur Source for the Construction of Isothiochromenes and Benzo[b]thiophenes by Copper-Catalyzed endo-Selective Hydrothiolation
We thank the JSPS KAKENHI Grant Number (JP19K05463). Also, this research was partially supported by Ogawa Sho research fund.
Abstract
A copper-catalyzed construction of isothiochromenes and benzo[b]thiophenes via annulation with 1,1,1,3,3,3-hexamethyldisilathiane as a sulfur source is described. In the isothiochromene synthesis, the use of the disilathiane as a sulfur source successfully controls the regioselectivity of cyclization to afford the isothiochromene as the sole product. The present strategy can be applied to the synthesis of 2-aryl/2-alkylbenzo[b]thiophenes.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1953-4534.
- Supporting Information
Publikationsverlauf
Eingereicht: 08. September 2022
Angenommen: 29. September 2022
Accepted Manuscript online:
29. September 2022
Artikel online veröffentlicht:
09. November 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Gawronski J, Wascinska N, Gajewy J. Chem. Rev. 2008; 108: 5227
- 1b Capperucci A, Degl’Innocenti A, Pollicino S, Acciai M, Castagnoli G, Malesci I, Tiberi C. Heteroat. Chem. 2007; 18: 516
- 1c Degl’Innocenti A, Capperucci A. Eur. J. Org. Chem. 2000; 2171
- 1d Hwu JR, Tsay S.-C. Chem. Commun. 1998; 161
- 1e Mizhiritskii MD, Reikhsfel’d VO. Russ. Chem. Rev. 1988; 57: 447
- 2a Tanini D, Angeli A, Capperucci A. Phosphorus, Sulfur Silicon Relat. Elem. 2015; 191: 156
- 2b Polshettiwar V, Kaushik MP. J. Sulfur Chem. 2006; 27: 353
- 2c Degl’Innocenti A, Capperucci A, Castagnoli G, Malesci I. Synlett 2005; 1965
- 2d Capperucci A, Degl’Innocenti A, Nocentini T, Castagnoli G, Malesci I, Cerreti A. Phosphorus, Sulfur Silicon Relat. Elem. 2005; 180: 1247
- 2e Degl’Innocenti A, Capperucci A, Nocentini T, Biondi S, Fratini V, Castagnoli G, Malesci I. Synlett 2004; 2159
- 2f Capperucci A, Degl’Innocenti A, Nocentini T, Biondi S, Dini F. J. Organomet. Chem. 2003; 686: 363
- 2g Capperucci A, Degl’Innocenti A, Biondi S, Nocentini T, Rinaudo G. Tetrahedron Lett. 2003; 44: 2831
- 2h Capperucci A, Degl’Innocenti A, Scafato P, Spagnolo P. Chem. Lett. 1995; 147
- 3a Detty MR, Seidler MD. J. Org. Chem. 1982; 47: 1354
- 3b Soysa HS. D, Weber WP. Tetrahedron Lett. 1978; 19: 235
- 4a Tsay S.-C, Gani P, Hwu JR. J. Chem. Soc., Perkin Trans. 1 1991; 1493
- 4b Hwu JR, Tsay S.-C. Tetrahedron 1990; 46: 7413
- 5a Kamal A, Reddy KL, Reddy GS. K, Reddy BS. N. Tetrahedron Lett. 2004; 45: 3499
- 5b Capperucci A, Degl’Innocenti A, Funicello M, Mauriello G, Scafato P, Spagnolo P. J. Org. Chem. 1995; 60: 2254
- 6a Capperucci A, Salles C, Scarpelli S, Tanini D. Phosphorus, Sulfur Silicon Relat. Elem. 2017; 192: 172
- 6b Dere RT, Kumar A, Kumar V, Zhu X, Schmidt RR. J. Org. Chem. 2011; 76: 7539
- 6c Lai L.-L, Lin P.-Y, Huang W.-H, Shiao M.-J, Hwu JR. Tetrahedron Lett. 1994; 35: 3545
- 6d Tsay S.-C, Lin L, Furth P, Shum C, King D, Yu S, Chen B.-L, Hwu J. Synthesis 1993; 329
- 6e Steliou K, Salama P, Corriveau J. J. Org. Chem. 1985; 50: 4969
- 7a Sakai N, Maeda H, Ogiwara Y. Synthesis 2019; 51: 2323
- 7b Ogiwara Y, Maeda H, Sakai N. Synlett 2017; 29: 655
- 8 Nakajima T, Takano K, Maeda H, Ogiwara Y, Sakai N. Chem. Asian J. 2021; 16: 4103
- 9 Graham CM. E, Pritchard TE, Boyle PD, Valjus J, Tuononen HM, Ragogna PJ. Angew. Chem. Int. Ed. 2017; 56: 6236
- 10a Abu-Hashem AA, Gouda MA, Badria FA. Med. Chem. Res. 2018; 27: 2297
- 10b Kaminskyy D, Kryshchyshyn A, Nektegayev I, Vasylenko O, Grellier P, Lesyk R. Eur. J. Med. Chem. 2014; 75: 57
- 10c Liu J, Birzin ET, Chan W, Yang YT, Pai L.-Y, DaSilva C, Hayes EC, Mosley RT, DiNinno F, Rohrer SP, Schaeffer JM, Hammond ML. Bioorg. Med. Chem. Lett. 2005; 15: 715
- 11a Spencer J, Pfeffer M, Kyritsakas N, Fischer J. Organometallics 1995; 14: 2214
- 11b Spencer J, Pfeffer M, DeCian A, Fischer J. J. Org. Chem. 1995; 60: 1005
- 11c Dupont J, Pfeffer M. J. Organomet. Chem. 1987; 321: C13
- 12 Urriolabeitia EP, Ruiz S. Org. Biomol. Chem. 2019; 17: 2542
- 13a Kobayashi K, Ueyama T, Horiuchi M. Heterocycles 2017; 94: 2065
- 13b Schneider C, Bortolatto C, Back D, Menezes P, Zeni G. Synthesis 2010; 413
- 13c Wada Y, Ichikawa J, Katsume T, Nohiro T, Okauchi T, Minami T. Bull. Chem. Soc. Jpn. 2001; 74: 971
- 14 Shi S, Sun L.-L, Liao Z.-Y, Zhang X.-G. Synthesis 2012; 44: 966
- 15 Sashida H, Kaname M, Nakayama A, Suzuki H, Minoura M. Tetrahedron 2010; 66: 5149
- 16 Feng J, Lv M, Lu G, Cai C. Eur. J. Org. Chem. 2014; 5312
- 17a Sangeetha S, Sekar G. Chem. Commun. 2020; 56: 10906
- 17b Moon S, Kato M, Nishii Y, Miura M. Adv. Synth. Catal. 2020; 362: 1669
- 17c Nguyen TB, Retailleau P. Org. Lett. 2018; 20: 186
- 17d Nguyen TB, Retailleau P. Org. Lett. 2017; 19: 4858
- 17e Kuhn M, Falk FC, Paradies J. Org. Lett. 2011; 13: 4100
- 17f Sun L.-L, Deng C.-L, Tang R.-Y, Zhang X.-G. J. Org. Chem. 2011; 76: 7546
- 17g Li C.-L, Zhang X.-G, Tang R.-Y, Zhong P, Li J.-H. J. Org. Chem. 2010; 75: 7037
- 18 When substrate 5a was treated with 5 mol% of CuCl and 1,10-phenanthroline in the presence of K2CO3, the corresponding product 6a was obtained in a nearly quantitative yield.
- 19 Substitution of a benzyl bromide with a disilathiane proceeds in the presence of a base, see: Ando W, Furuhata T, Tsumaki H, Sekiguchi A. Synth. Commun. 1982; 12: 627
- 20 Liu Y, Kim J, Seo H, Park S, Chae J. Adv. Synth. Catal. 2015; 357: 2205
- 21 Gade T, Streek M, Voß J. Chem. Ber. 1992; 125: 127
- 22 Vechorkin O, Proust V, Hu X. Angew. Chem. Int. Ed. 2010; 49: 3061
- 23 Guilarte V, Fernández-Rodríguez MA, García-García P, Hernando E, Sanz R. Org. Lett. 2011; 13: 5100
- 24 Li Y, Cheng L, Jiang S, Chen L, Shao Y. ChemistrySelect 2016; 5: 1092