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 2018; 50(03): 565-574
DOI: 10.1055/s-0036-1591849
DOI: 10.1055/s-0036-1591849
paper
Indium-Catalyzed Direct Conversion of Lactones into Thiolactones and Selenolactones in the Presence of Elemental Sulfur and Selenium
This work was partially supported by JSPS KAKENHI grant number JP25410120.Further Information
Publication History
Received: 06 October 2017
Accepted after revision: 07 November 2017
Publication Date:
14 December 2017 (online)
Abstract
The direct conversion of lactones into thiolactones with elemental sulfur (S8) catalyzed by InCl3/PhSiH3 in a one-pot reaction is described. This catalytic system was successfully applied to the novel preparation of selenolactones from lactones and selenium.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591849.
- Supporting Information
-
References
- 1a Jones BA. Bradshaw JS. Chem. Rev. 1984; 84: 17
- 1b Larik FA. Saeed A. Muqadar U. El-Seedi H. Faisal M. Channar PA. Mehfooz H. Phosphorus, Sulfur Silicon Relat. Elem. 2017; 192: 490
- 2 For example: Ertas E. Ozturk T. Tetrahedron Lett. 2004; 45: 3405 ; and references cited therein
- 3a Scheibye S. Kristensen J. Lawesson SO. Tetrahedron 1979; 35: 1339
- 3b Cava MP. Levinson MI. Tetrahedron 1985; 41: 5061
- 4 For a selected paper on the conversion of lactones into thionolactones with Lawesson’s reagent, see: Clyne DS. Weiler L. Tetrahedron 1999; 55: 13659
- 5a Rioult P. Vialle J. Bull. Soc. Chim. Fr. 1965; 3312
- 5b Nader RB. Kaloustian MK. Tetrahedron Lett. 1979; 20: 1477
- 5c Kaloustian MK. Khouri F. Tetrahedron Lett. 1981; 22: 413
- 5d Curphey TJ. J. Org. Chem. 2002; 67: 6461
- 5e Cho D. Ahn J. De Castro KA. Ahn H. Rhee H. Tetrahedron 2010; 66: 5583
- 5f Yang C.-H. Li G.-J. Gong C.-J. Li Y.-M. Tetrahedron 2015; 71: 637
- 5g Ozturk T. Ertas E. Mert O. Chem. Rev. 2010; 110: 3419 ; and references cited therein
- 6 Zhan X.-Q. Qian Z.-H. Zheng H. Su B.-Y. Lan Z. Xu J.-G. Chem. Commun. 2008; 1859
- 7 Gerecke M. Zimmermann JP. Aschwanden W. Helv. Chim. Acta 1970; 53: 991
- 8a Fries K. Mengel H. Ber. Dtsch. Chem. Ges. 1912; 45: 3408
- 8b For isomerization of thionolactones to thiolactones with a Lewis acid, see also: Filippi J.-J. Fernandez X. Duñach E. Tetrahedron Lett. 2006; 47: 6067
- 8c Oparin DA. Kuznetsova AS. Chem. Heterocycl. Compd. 1991; 27: 139
- 9 For a report on an in situ formation of a disilathiane from S8 and a hydrosilane in the presence of an In(III) compound, see: Miyazaki T. Nishino K. Yoshimoto S. Ogiwara Y. Sakai N. Eur. J. Org. Chem. 2015; 1991
- 10a Miura K. Yamada Y. Tomita M. Hosomi A. Synlett 2004; 1985
- 10b Sakai N. Moriya T. Konakahara T. J. Org. Chem. 2007; 72: 5920
- 10c Tsuchimoto T. Igarashi M. Aoki K. Chem. Eur. J. 2010; 16: 8975
- 10d Pehlivan L. Métay E. Delbrayelle D. Mignani G. Lemaire M. Eur. J. Org. Chem. 2012; 4689
- 10e Moriya T. Yoneda S. Kawana K. Ikeda R. Konakahara T. Sakai N. J. Org. Chem. 2013; 78: 10642
- 10f Inamoto Y. Kaga Y. Nishimoto Y. Yasuda M. Baba A. Org. Lett. 2013; 15: 3452
- 10g Ogiwara Y. Uchiyama T. Sakai N. Angew. Chem. Int. Ed. 2016; 55: 1864
- 10h Nomiyama S. Hondo T. Tsuchimoto T. Adv. Synth. Catal. 2016; 358: 1136
- 11 Sakai N. Horikawa S. Ogiwara Y. RSC Adv. 2016; 6: 81763
- 12 When γ-butyrolactone (1a) was treated with several hydrosilanes, such as Ph2MeSiH, Et3SiH, and TMDS (tetramethyldisiloxane) in the presence of InCl3, the corresponding γ-butyrothiolactone (2a) was obtained in 4, 9, and 25% yields, respectively.
- 13a Moriya T. Yoneda S. Kawana K. Ikeda R. Konakahara T. Sakai N. Org. Lett. 2012; 14: 4842
- 13b Sakai N. Asama S. Anai S. Konakahara T. Tetrahedron 2014; 70: 2027
- 13c Sakai N. Takeoka M. Kumaki T. Asano H. Konakahara T. Ogiwara Y. Tetrahedron Lett. 2015; 56: 6448
- 14a Freudendahl DM. Shahzad SA. Wirth T. Eur. J. Org. Chem. 2009; 1649
- 14b Wirth T. Angew. Chem. Int. Ed. 2000; 39: 3740
- 14c Wirth T. Tetrahedron 1999; 55: 1
- 14d Baird CP. Rayner CM. J. Chem. Soc., Perkin Trans. 1 1998; 1973
- 15a Lemaire C. Luxen A. Christiaens L. Guillaume M. J. Heterocycl. Chem. 1983; 20: 811
- 15b Sashida H. Nakayama A. Kaname M. Synthesis 2008; 3229
- 16 For a recent example on the preparation of 2-selenopyrones and selenocoumarins, see: Murai T. Yoshida A. Mizutani T. Kubuki H. Yamaguchi K. Maruyama T. Shibahara F. Chem. Lett. 2017; 46: 1017
- 17 On the basis of our previous work on in situ generation of a disilathiane derived from S8 and a hydrosilane in the presence of InI3,9 we performed the following control experiment. When adding lactone 1a to the resultant solution consisting of the disilathiane, which was prepared from S8 and PhSiH3 in the presence of 5 mol % of InCl3 under o-DCB reflux conditions (3 h), thiolactone 2a was obtained in an 84% GC yield. The result further supported that a disilathiane is a key intermediate in the series of conversions.
- 18 As the control experiment, when a thionolactone, dihydro-5-phenyl-2(3H)-furanthionone, was treated with only 5 mol% of InCl3, the quantitative formation of thiolactone 1a was observed as well as the result reported by Duñach et al.8b Therefore, there may be a third pathway of the direct conversion of a lactone into a thiolactone via a thionolactone intermediate, besides to our proposed pathways shown in Scheme 5. However, during our investigations we have not found any trace of the corresponding thionolactone intermediate in the cross-over reaction between a γ-lactone and a disilathiane at all.
- 19a Degl’Innocenti A. Ulivi P. Capperucci A. Reginato G. Mordini A. Ricci A. Synlett 1992; 883
- 19b Nishimoto Y. Okita A. Yasuda M. Baba A. Org. Lett. 2012; 14: 1846
- 19c Nishino K. Minato K. Miyazaki T. Ogiwara Y. Sakai N. J. Org. Chem. 2017; 82: 3659
- 20a For report on a nucleophilic substitution of a benzyl silyl ether with either a benzyl silyl thioether or a dithiasilane, leading to a dibenzyl thioether, see: Miyazaki T. Katayama M. Yoshimoto S. Ogiwara Y. Sakai N. Tetrahedron Lett. 2016; 57: 676
- 20b See also ref. 9.
- 21 Sakai N. Kobayashi T. Ogiwara Y. Chem. Lett. 2015; 44: 1503
- 22 Grover HK. Emmett MR. Kerr MA. Org. Lett. 2013; 15: 4838
- 23 Dohi T. Takenaga N. Goto A. Maruyama A. Kita Y. Org. Lett. 2007; 9: 3129
- 24 Pirkle WH. Spence PL. J. Chromatogr. A 1997; 775: 81
- 25 Kobayashi K. Shigemura Y. Ezaki K. Heterocycles 2015; 91: 526
- 26 Almena J. Foubelo F. Yus M. J. Org. Chem. 1996; 61: 1859
- 27 Baig N. Sai Sudhir RB. V. Chandrasekaran S. Synlett 2008; 2684
For example:
For selected papers on the conversion of lactones (or esters) into thionolactones (or thionoesters) without Lawesson’s reagent, see:
For selected papers on In(III)-catalyzed transformation of carbonyl compounds in the presence of a hydrosilane, see:
For selected reviews on oraganoselenium chemistry, see:
For papers on the preparation of selenolactones with NaSeH, see:
For selected papers on the addition or substitution of a thiosilane with electrophiles, see: