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Synlett 2022; 33(20): 2026-2032
DOI: 10.1055/a-1928-7308
DOI: 10.1055/a-1928-7308
letter
A Reductive Benzylation for Benzenes Using Aroyl Chlorides and Triethylsilane Catalyzed by Aluminosilicate-Stabilized Silyl Cations on Montmorillonite
Financial supports from the Japan Society for the Promotion of Science (JSPS KAKENHI Grant number JP19K05157) and the White Rock Foundation are gratefully acknowledged.
Abstract
We discovered that the aluminosilicate-stabilized silyl cations, which were created from a solid-acid catalyst, the proton-exchanged montmorillonite, and Et3SiH, efficiently promoted the reductive benzylation of benzenes with aromatic carboxylic acid chlorides and Et3SiH in one pot.
Key words
montmorillonite aluminosilicate-stabilized silyl cations - proton-exchanged montmorillonite - benzoyl chlorides - Et3SiH - benzylation of benzenes - one-pot reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1928-7308.
- Supporting Information
Publikationsverlauf
Eingereicht: 22. Juni 2022
Angenommen nach Revision: 22. August 2022
Accepted Manuscript online:
22. August 2022
Artikel online veröffentlicht:
11. Oktober 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
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References
- 1a Chiche B, Finiels A, Gauthier C, Geneste P, Graille J, Pioch D. J. Mol. Catal. 1987; 42: 229
- 1b Ferris JP, Ertem G. Science 1992; 257: 1387
- 1c Cramarossa MR, Forti L, Ghelfi F. Tetrahedron 1997; 53: 15889
- 1d Kawabata T, Mizugaki T, Ebitani K, Kaneda K. J. Am. Chem. Soc. 2003; 125: 10486
- 1e Hara N, Nakamura S, Shibata N, Torua T. Adv. Synth. Catal. 2010; 352: 1621
- 1f Vellayan K, González B, Trujillano R, Vicente MA, Gil A. Appl. Clay Sci. 2018; 160: 126
- 2a Izumi Y, Onaka M. Adv. Catal. 1992; 38: 245
- 2b Pinnavaia TJ. Science 1983; 220: 365
- 2c Ballantine JM, Purnell JH, Thomas JM. J. Mol. Catal. 1984; 27: 157
- 3 Onaka M, Higuchi K, Nanami H, Izumi Y. Bull. Chem. Soc. Jpn. 1993; 66: 2638
- 4 Tandiary MA, Masui Y, Onaka M. Tetrahedron Lett. 2014; 55: 4160
- 5 Klare HF. T, Albers L, Susse L, Keess S, Muller T, Oestreich M. Chem. Rev. 2021; 121: 5889
- 6a Lambert JB, Zhang S. J. Chem. Soc., Chem. Commun. 1993; 383
- 6b Lambert JB, Zhang S, Stern CL, Huffman JC. Science 1993; 260: 1917
- 6c Lambert JB, Zhang S, Ciro SM. Organometallics 1994; 13: 2430
- 6d Lambert JB, Zhao Y. Angew. Chem., Int. Ed. Engl. 1997; 36: 400
- 6e Lambert JB, Zhao Y, Wu H, Tse WC, Kuhlmann B. J. Am. Chem. Soc. 1999; 121: 5001
- 6f Lambert JB, Lin L. J. Org. Chem. 2001; 66: 8537
- 6g Müller T. Angew. Chem. Int. Ed. 2001; 40: 3033
- 6h Ichinohe M, Igarashi M, Sanuki K, Sekiguchi A. J. Am. Chem. Soc. 2005; 127: 9978
- 6i Inoue S, Ichinohe M, Yamaguchi T, Sekiguchi A. Organometallics 2008; 27: 6056
- 6j Schäfer A, Reißmann M, Schäfer A, Saak W, Haase D, Müller T. Angew. Chem. Int. Ed. 2011; 50: 12636
- 6k Gerdes C, Saak W, Haase D, Müller T. J. Am. Chem. Soc. 2013; 135: 10353
- 6l Albers L, Baumgartner J, Marschner C, Mìller T. Chem. Eur. J. 2016; 22: 7970
- 6m Fernandes A, Laye C, Pramanik S, Palmeira D, Pekel ÖÖ, Massip S, Schmidtmann M, Müller T, Robert F, Landais Y. J. Am. Chem. Soc. 2020; 142: 564
- 7a Reed CA, Xie Z, Bau R, Benesi A. Science 1993; 262: 402
- 7b Xie Z, Liston DJ, Jelinek T, Mitro V, Bau R, Reed CA. J. Chem. Soc., Chem. Commun. 1993; 384
- 7c Reed CA, Xie Z. Science 1994; 263: 985
- 7d Xie Z, Bau R, Benesi A, Reed CA. Organometallics 1995; 14: 3933
- 7e Xie Z, Manning J, Reed RW, Mathur R, Boyd PD. W, Benesi A, Reed CA. J. Am. Chem. Soc. 1996; 118: 2922
- 7f Reed CA. Chem. Commun. 2005; 1669
- 7g Hoffmann SP, Kato T, Tham FS, Reed CA. Chem. Commun. 2006; 767
- 7h Küppers T, Bernhardt E, Eujen R, Willner H, Lehmann CW. Angew. Chem. Int. Ed. 2007; 46: 6346
- 7i Omann L, Pudasaini B, Irran E, Klare HF. T, Baik M.-H, Oestreich M. Chem. Sci. 2018; 9: 5600
- 7j Wu Q, Irran E, Müller R, Kaupp M, Klare HF. T, Oestreich M. Science 2019; 365: 168
- 8a Scott VJ, Çelenligil-Çetin R, Ozerov OV. J. Am. Chem. Soc. 2005; 127: 2852
- 8b Panisch R, Bolte M, Müller T. J. Am. Chem. Soc. 2006; 128: 9676
- 8c Meier G, Braun T. Angew. Chem. Int. Ed. 2009; 48: 1546
- 8d Duttwyler S, Douvris C, Fackler NL. P, Tham FS, Reed CA, Baldridge KK, Siegel JS. Angew. Chem. Int. Ed. 2010; 49: 7519
- 8e Lühmann N, Panisch R, Müller T. Appl. Organomet. Chem. 2010; 24: 533
- 8f Allemann O, Duttwyler S, Romanato P, Baldridge KK, Siegel JS. Science 2011; 332: 574
- 8g Stahl T, Klare HF. T, Oestreich M. ACS Catal. 2013; 3: 1578
- 8h Mallov I, Ruddy AJ, Zhu H, Grimme S, Stephan DW. Chem. Eur. J. 2017; 23: 17692
- 8i Shao B, Bagdasarian AL, Popov S, Nelson HM. Science 2017; 355: 1403
- 9 Sakai N, Kawana K, Ikeda R, Nakaike Y, Konakahara T. Eur. J. Org. Chem. 2011; 17: 3178
- 10 Moriya T, Takayama K, Konakahara T, Ogiwara Y, Sakai N. Eur. J. Org. Chem. 2015; 2277
- 11a Aizpurua JM, Lecea B, Palomo C. Can. J. Chem. 1986; 64: 2342
- 11b Miyai T, Onishi Y, Baba A. Tetrahedron Lett. 1998; 39: 6291
- 11c Miyai T, Onishi Y, Baba A. Tetrahedron 1999; 55: 1017
- 11d Shiina I, Suzuki M, Yokoyama K. Tetrahedron Lett. 2002; 43: 6395
- 11e Chandrasekhar S, Khatun S, Rajesh G, Reddy CR. Tetrahedron Lett. 2009; 50: 6693
- 11f Savela R, Majewski M, Leino R. Eur. J. Org. Chem. 2014; 4137
- 11g Parnes R, Pappo D. Org. Lett. 2015; 17: 2924
- 12a West CT, Donnelly SJ, Kooistra DA, Doyle MP. J. Org. Chem. 1973; 38: 2675
- 12b Gevorgyan V, Rubin M, Liu J.-X, Yamamoto Y. J. Org. Chem. 2001; 66: 1672
- 12c Bajracharya GB, Nogami T, Jin T, Matsuda K, Gevorgyan V, Yamamoto Y. Synthesis 2004; 308
- 12d Bach P, Albright A, Laali KK. Eur. J. Org. Chem. 2009; 1961
- 13 Takehira S, Masui Y, Onaka M. Chem. Lett. 2014; 43: 498 . And see for the supporting information
- 14a Masui Y, Wang J, Teramura K, Kogure T, Tanaka T, Onaka M. Micropor. Mesopor. Mater. 2014; 198: 129
- 14b Wang J, Masui Y, Watanabe K, Onaka M. Adv. Synth. Catal. 2009; 351: 553
- 14c Wang J, Masui Y, Onaka M. Eur. J. Org. Chem. 2010; 1763
- 14d Wang J, Masui Y, Onaka M. Appl. Catal. B 2011; 107: 135
- 14e Wang J, Masui Y, Onaka M. ACS Catal. 2011; 1: 446
- 14f Tandiary MA, Asano M, Hattori T, Takehira S, Masui Y, Onaka M. Tetrahedron Lett. 2017; 58: 1925