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 2014; 46(02): 195-202
DOI: 10.1055/s-0033-1338563
DOI: 10.1055/s-0033-1338563
paper
Catalytic C–H Activation of Arylacetylenes: A Fast Assembly of 3-(Arylethynyl)-3-hydroxyindolin-2-ones Using CuI/DBU
Weitere Informationen
Publikationsverlauf
Received: 27. August 2013
Accepted after revision: 29. Oktober 2013
Publikationsdatum:
28. November 2013 (online)
Abstract
A highly efficient and atom-economic methodology has been developed for the synthesis of 3-(arylethynyl)-3-hydroxyindolin-2-ones from isatins by C–H activation of arylacetylenes using a catalytic quantity of copper(I) iodide (5 mol%) and DBU (20 mol%) at 25 °C, affording the products in excellent yields in very short reaction time (5 min).
Key words
catalysis - C–H activation - copper(I) iodide - arylalkyne addition - 3-hydroxyindolin-2-onesSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis. Included are scanned spectra (IR, 1H NMR, 13C NMR and HRMS).
- Supporting Information
-
References
- 1a Frantz DE, Fässler R, Tomooka CS, Carreira EM. Acc. Chem. Res. 2000; 33: 373
- 1b Li CJ. Acc. Chem. Res. 2010; 43: 581
- 1c Fujimori S, Knöpfel TF, Zarotti P, Ichikawa T, Boyall D, Carreira EM. Bull. Chem. Soc. Jpn. 2007; 80: 1635
- 1d Trost BM, Weiss AH. Adv. Synth. Catal. 2009; 351: 963
- 2 Kumagai N, Matsunaga S, Shibasaki M. J. Am. Chem. Soc. 2004; 126: 13632 ; and references cited therein
- 3a Cozzi PG, Hilgraf R, Zimmermann N. Eur. J. Org. Chem. 2004; 4095
- 3b Modern Acetylene Chemistry . Diederich F, Stang PJ. VCH; Weinheim: 1995
- 4a Marshall JA, Bourbeau MP. Org. Lett. 2003; 5: 3197
-
4b Siemsen P, Livingston RC, Diederich F. Angew. Chem. Int. Ed. 2000; 39: 2632
- 5a Sarciron ME, Audin P, Delabre I, Gabrion C, Petavy AF, Paris J. J. Pharm. Sci. 1993; 82: 605
- 5b Brummond KM, Osbourn JM. Beilstein J. Org. Chem. 2010; 6: 33
- 5c Dong Y.-W, Wang G.-W, Wang L. Tetrahedron 2008; 64: 10148
- 6a Makaiyama T, Suzuki K, Sato T. Chem. Lett. 1979; 447
- 6b Tombo GM. R, Didier E, Loubinoux B. Synlett 1990; 547
- 6c Frantz DE, Fässler R, Carreira EM. J. Am. Chem. Soc. 2000; 122: 1806
- 6d Sasaki H, Boyall D, Carreira EM. Helv. Chim. Acta 2001; 84: 964
- 6e Tan L, Chen C.-Y, Tillyer RD, Grabowski EJ. J, Reider PJ. Angew. Chem. Int. Ed. 1999; 38: 711
- 7a Anand NK, Carreira EM. J. Am. Chem. Soc. 2001; 123: 9687
- 7b Moor D, Lin P. Org. Lett. 2002; 4: 1855
- 7c Li X, Lu G, Kwok WH, Chan AS. C. J. Am. Chem. Soc. 2002; 124: 12636
-
8 Huang B, Yao X, Li C.-J. Adv. Synth. Catal. 2006; 348: 1528
- 9 Tzalis D, Knochel P. Angew. Chem. Int. Ed. 1999; 38: 1463
- 10 Pereshivko OP, Peshkov VA, Van der Eycken EV. Org. Lett. 2010; 12: 2638
- 11 Boyall D, Lopez F, Sasaki H, Frantz DE, Carreira EM. Org. Lett. 2000; 2: 4233
- 12 Sato I, Saito T, Soai K. Chem. Commun. 2000; 2471
- 13 Xu Z, Chen C, Xu J, Miao M, Yan W, Wang R. Org. Lett. 2004; 6: 1193
- 14a Ried W, Suarez-Rivero E. Chem. Ber. 1963; 96: 1475
- 14b Chen G, Wang Y, Gao S, He H.-P, Li S.-L, Zhang J.-X, Ding J, Hao X.-J. J. Heterocycl. Chem. 2009; 46: 217
- 14c Fu X.-P, Liu L, Wang D, Chena Y.-J, Li C.-J. Green Chem. 2011; 13: 549
- 15 Peddibhotla S. Curr. Bioact. Compd. 2009; 5: 20 ; and references cited therein
- 16 Boechat N, Kover WB, Bongertz V, Bastos MM, Romeiro NC, Azevedo ML. G, Wollinger W. Med. Chem. 2007; 3: 533
- 17a Kumar V, Khatik GL, Nair VA. Synlett 2011; 2997
- 17b Chouhan M, Sharma R, Nair VA. Appl. Organomet. Chem. 2011; 25: 470
- 17c Khatik GL, Khurana R, Kumar V, Nair VA. Synthesis 2011; 3123
- 17d Kumar V, Khatik GL, Pal A, Praneeth MR, Bhattarai S, Nair VA. Synlett 2012; 23: 2357
- 17e Khatik GL, Kumar V, Nair VA. Org. Lett. 2012; 14: 2442
- 17f Chouhan M, Sharma R, Nair VA. Org. Lett. 2012; 14: 5672
- 17g Kumar V, Kumar K, Pal A, Khatik GL, Nair VA. Tetrahedron 2013; 69: 1747
- 17h Gahtory D, Chouhan M, Sharma R, Nair VA. Org. Lett. 2013; 15: 3942