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 2013; 45(15): 2093-2100
DOI: 10.1055/s-0033-1338797
DOI: 10.1055/s-0033-1338797
special topic
Polymeric Bimetallic Catalyst-Promoted In-Water Dehydrative Alkylation of Ammonia and Amines with Alcohols
Weitere Informationen
Publikationsverlauf
Received: 19. Februar 2013
Accepted after revision: 14. April 2013
Publikationsdatum:
29. Mai 2013 (online)
![](https://www.thieme-connect.de/media/synthesis/201315/lookinside/thumbnails/10.1055-s-0033-1338797-1.jpg)
Abstract
A dehydrative alkylation with three kinds of Ir/B heterobimetallic polymeric catalysts in water is reported. The polymeric heterobimetallic catalysts were readily prepared by ionic convolution of a poly(catechol borate) and iridium complexes. The N-alkylation of ammonia and amines with alcohols, as alkylating agents, was carried out with a heterogeneous catalyst (1 mol% Ir) at 100 °C without the use of organic solvents under aerobic and aqueous conditions to afford the corresponding alkylated amines in high yield.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Alberts B, Johnson A, Lewis J, Raff M, Roberts K, Walter P. Molecular Biology of the Cell . 5th ed. Garland Science; New York: 2008
- 1b The RNA World . Gesteland RF, Cech T, Atkins JF. 3rd ed. Cold Spring Harbor Laboratory Press; Cold Spring Harbor: 2005
- 2 Tooley CE. S, Petkowski JJ, Muratore-Schroeder TL, Balsbaugh JL, Shabanowitz J, Sabat M, Minor W, Hunt DF, Macara IG. Nature 2010; 466: 1125
- 3a Organic Synthesis in Water . Grieco PA. Blackie Academic and Professional; London: 1998
- 3b Li C.-J. Chem. Rev. 1993; 93: 2023
- 3c Ishihara K. Tetrahedron 2009; 65: 1085
- 4 For a review, see: Nicolaou KC, Snyder SA. Classics in Total Synthesis II . Wiley-VCH; Weinheim: 2003
- 5a Fujita K, Yamaguchi R. Synlett 2005; 560
- 5b Hamid MH. S. A, Slatford PA, Williams JM. J. Adv. Synth. Catal. 2007; 349: 1555
- 5c Guillena G, Ramón DJ, Yus M. Angew. Chem. Int. Ed. 2007; 46: 2358
- 5d Nixon TD, Whittlesey MK. J, Williams MJ. Dalton Trans. 2009; 753
- 5e Dobereiner GE, Crabtree RH. Chem. Rev. 2010; 110: 681
- 5f Guillena G, Ramón DJ, Yus M. Chem. Rev. 2010; 110: 1611
- 5g Watson AJ. A, Williams JM. J. Science 2010; 329: 635
- 5h Crabtree RH. Organometallics 2011; 30: 17
- 6a Fujita K, Yamamoto K, Yamaguchi R. Org. Lett. 2002; 4: 2691
- 6b Cami-Kobeci G, Slatford PA, Whittlesey MK, Williams JM. J. Bioorg. Med. Chem. Lett. 2005; 15: 535
- 6c Eary CT, Clausen D. Tetrahedron Lett. 2006; 47: 6899
- 6d Prades A, Corberán R, Poyatos M, Peris E. Chem. Eur. J. 2008; 14: 11474
- 6e Aramoto H, Obora Y, Ishii Y. J. Org. Chem. 2009; 74: 628
- 6f Chang Y.-H, Fu C.-F, Liu Y.-H, Peng S.-M, Chen J.-T, Liu S.-T. Dalton Trans. 2009; 861
- 6g Blank B, Michlik S, Kempe R. Chem. Eur. J. 2009; 15: 3790
- 6h Liu S, Rebros M, Stephens G, Marr AC. Chem. Commun. 2009; 2308
- 7a Watanabe Y, Tsuji Y, Ohsugi Y. Tetrahedron Lett. 1981; 22: 2667
- 7b Murahashi S.-I, Kondo K, Hakata T. Tetrahedron Lett. 1982; 23: 229
- 7c Arcelli A, Khai BT, Porzi G. J. Organomet. Chem. 1982; 235: 93
- 7d Watanabe Y, Tsuji Y, Ige H, Ohsugi Y, Ohta T. J. Org. Chem. 1984; 49: 3359
- 7e Marsella JA. J. Org. Chem. 1987; 52: 467
- 7f Watanabe Y, Morisaki Y, Kondo T, Mitsudo T.-a. J. Org. Chem. 1996; 61: 4214
- 7g Abbenhuis RA. T. M, Boersma J, van Koten G. J. Org. Chem. 1998; 63: 4282
- 7h Bitsi G, Schleiffer E, Antoni F, Jenner G. J. Organomet. Chem. 1989; 373: 343
- 7i Del Zotto A, Baratta W, Sandri M, Verardo G, Rigo P. Eur. J. Inorg. Chem. 2004; 524
- 7j Tillack A, Hollmann D, Michalik D, Beller M. Tetrahedron Lett. 2006; 47: 8881
- 7k Hamid MH. S. A, Allen CL, Lamb GW, Maxwell AC, Maytum HC, Watson AJ. A, Williams JM. J. J. Am. Chem. Soc. 2009; 131: 1766
- 8a Nordstrøm LU, Madsen R. Chem. Commun. 2007; 5034
- 8b Gunanathan C, Milstein D. Angew. Chem. Int. Ed. 2008; 47: 8661
- 8c Kawahara R, Fujita K, Yamaguchi R. J. Am. Chem. Soc. 2010; 132: 15108
- 8d Saidi O, Blacker AJ, Farah MM, Marsden SP, Williams JM. J. Chem. Commun. 2010; 46: 1541
- 8e Saidi O, Blacker AJ, Lamb GW, Marsden SP, Taylor JE, Williams JM. J. Org. Process Res. Dev. 2010; 14: 1046
- 8f Kawahara R, Fujita K, Yamaguchi R. Adv. Synth. Catal. 2011; 353: 1161
- 9a Narayanan S, Deshpande K. Appl. Catal., A 2000; 199: 1
- 9b Valotl F, Fachel F, Jacquot R, Spagnol M, Lemairel M. Tetrahedron Lett. 1999; 40: 3689
- 9c Martínez R, Ramón DJ, Yus M. Org. Biomol. Chem. 2009; 7: 2176
- 9d Kim JW, Yamaguchi K, Mizuno N. J. Catal. 2009; 263: 205
- 9e Kwon MS, Kim S, Park S, Bosco W, Chidrala RK, Park J. J. Org. Chem. 2009; 74: 2877
- 10a Yamada YM. A, Sarkar SM, Uozumi Y. J. Am. Chem. Soc. 2012; 134: 9285
- 10b Yamada YM. A, Sarkar SM, Uozumi Y. J. Am. Chem. Soc. 2012; 134: 3190
- 10c Sarkar SM, Uozumi Y, Yamada YM. A. Angew. Chem. Int. Ed. 2011; 50: 9437
- 10d Yamada YM. A, Jin C.-K, Uozumi Y. Org. Lett. 2010; 12: 4540
- 10e Yamada YM. A, Watanabe T, Torii K, Uozumi Y. Chem. Commun. 2009; 5594
- 10f Yamada YM. A, Guo H, Uozumi Y. Org. Lett. 2007; 9: 1501
- 10g Yamada YM. A, Uozumi Y. Tetrahedron 2007; 63: 8492
- 10h Uozumi Y, Yamada YM. A, Beppu T, Fukuyama N, Ueno M, Kitamori T. J. Am. Chem. Soc. 2006; 128: 15994
- 10i Yamada YM. A, Maeda Y, Uozumi Y. Org. Lett. 2006; 8: 4259
- 10j Yamada YM. A, Uozumi Y. Org. Lett. 2006; 8: 1375
- 11a Shibasaki M, Kanai M, Matsunaga S, Kumagai N. Acc. Chem. Res. 2009; 42: 1117
- 11b Shibasaki M, Kanai M, Funabashi K. Chem. Commun. 2002; 1989
- 11c Shibasaki M, Yoshikawa N. Chem. Rev. 2002; 102: 2187
- 11d Shibasaki M, Sasai H, Arai T. Angew. Chem., Int. Ed. Engl. 1997; 36: 1236
- 11e Wheatley N, Kalck P. Chem. Rev. 1999; 99: 3379
- 11f van den Beuken EK, Feringa BL. Tetrahedron 1998; 54: 12985
- 11g Handa S, Gnanadesikan V, Matsunaga S, Shibasaki M. J. Am. Chem. Soc. 2010; 132: 4925
- 11h Iwata M, Yazaki R, Suzuki Y, Kumagai N, Shibasaki M. J. Am. Chem. Soc. 2009; 131: 18244
- 11i Nitabaru T, Nojiri A, Kobayashi M, Kumagai N, Shibasaki M. J. Am. Chem. Soc. 2009; 131: 13860
- 12a Wang Z, Chen G, Ding K. Chem. Rev. 2009; 109: 322
- 12b Lu J, Toy PH. Chem. Rev. 2009; 106: 815
- 12c Takizawa S, Somei H, Jayaprakash D, Sasai H. Angew. Chem. Int. Ed. 2003; 42: 5711
- 12d Ding K, Wang Z, Wang X, Liang Y, Wang X. Chem. Eur. J. 2006; 12: 5188
- 12e Arai T, Sekiguchi T, Otsuki K, Takizawa S, Sasai H. Angew. Chem. Int. Ed. 2003; 42: 2144
- 13 Partial results have been reported as a rapid communication, see: Ohta H, Yuyama Y, Uozumi Y, Yamada Yoichi MA. Org. Lett. 2011; 12: 3892
- 14a Lang A, Knizek J, Nöth H, Schur S, Thomann M. Z. Anorg. Allg. Chem. 1997; 623: 901
- 14b Chikkali SH, Gudat D, Lissner F, Nieger M, Schleid T. Dalton Trans. 2007; 3906
- 15a Maki T, Ishihara K, Yamamoto H. Tetrahedron 2007; 63: 8645
- 15b Ishihara K, Kurihara H, Matsumoto M, Yamamoto H. J. Am. Chem. Soc. 1998; 120: 6920
- 16 Danjo H, Hirata K, Yoshigai S, Azumaya I, Yamaguchi K. J. Am. Chem. Soc. 2009; 131: 1638
- 17 See the experimental section for the preparation of 2.
- 18 See the experimental section for the preparation of 1·NEt3.
- 19 In the reaction mixture, iridium species were detected (0.008%; ICP-AES analysis).
- 20 The reaction in H2O at 100–150 °C without the use of microwaves was sluggish.
- 21 Abe T, Haga T, Negi S, Morita Y, Takayanagi K, Hamamura K. Tetrahedron 2001; 57: 2701
- 22 Imm S, Bähn S, Neubert L, Neumann H, Beller M. Angew. Chem. Int. Ed. 2010; 49: 8126
- 23 Pingen D, Müller C, Vogt D. Angew. Chem. Int. Ed. 2010; 49: 8130
- 24 Pangborn AB, Giardello MA, Grubbs RH, Rosen RK, Timmers FJ. Organometallics 1996; 15: 1518
For reviews, see:
For reviews, see:
For reactions using Ir catalysts, see:
For reactions using Ru, Rh, and Pt catalysts, see:
For homogeneous catalysis in water, see:
For heterogeneous catalysis in organic solvents, see: Review:
Examples:
For reviews on Shibasaki’s homogeneous heterobimetallic multifunctional catalysts, see:
For recent examples, see:
For reviews on heterobimetallic self-supported catalysts, see:
For examples, see:
For an example of the catalyst analogue concept, see: