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Synthesis 2018; 50(02): 278-281
DOI: 10.1055/s-0036-1588580
DOI: 10.1055/s-0036-1588580
psp
Scalable Synthesis of Hydrido-Disiloxanes from Silanes: A One-Pot Preparation of 1,3-Diphenyldisiloxane from Phenylsilane
Weitere Informationen
Publikationsverlauf
Received: 02. September 2017
Accepted after revision: 06. September 2017
Publikationsdatum:
26. September 2017 (online)
Abstract
A simple, one-pot, and high-yielding synthesis of 1,3-diphenyldisiloxane is presented. The preparation of similar symmetrical disiloxane materials is also accomplished with this same protocol. This mechano-chemical procedure is efficient and highly scalable, furnishing a convenient route to hydrido-disiloxanes from widely accessible commercially available silanes.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588580.
- Supporting Information
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References
- 1a Fritzsche H. Hasserodt U. Korte F. Friese G. Adrian K. Chem. Ber. 1965; 98: 171
- 1b Horner L. Balzer WD. Tetrahedron Lett. 1965; 1157
- 1c Marsi KL. J. Org. Chem. 1974; 39: 265
- 1d Hérault D. Nguyen DH. Nuel D. Buono G. Chem. Soc. Rev. 2015; 44: 2508
- 2a O’Brien CJ. Tellez JL. Nixon ZS. Kang LJ. Carter AL. Kunkel SR. Przeworski KC. Chass GA. Angew. Chem. Int. Ed. 2009; 48: 6836
- 2b van Kalkeren HA. te Grotenhuis C. Haasjes FS. Hommersom CR. A. Rutjes FP. J. T. van Delft FL. Eur. J. Org. Chem. 2013; 7059
- 2c van Kalkeren HA. Leenders SH. A. M. Hommersom CR. A. Rutjes FP. J. T. van Delft FL. Chem. Eur. J. 2011; 17: 11290
- 2d Zhao W. Yan PK. Radosevich AT. J. Am. Chem. Soc. 2015; 137: 616
- 2e Buonomo JA. Aldrich CC. Angew. Chem. Int. Ed. 2015; 54: 13041
- 3a Buonomo JA. Eiden CG. Aldrich CC. Chem. Eur. J. 2017; DOI: 10.1002/chem.201703875.
- 3b Buonomo JA. Cole M. Aldrich CC. unpublished results.
- 4a Tse FL. S. Chang T. Finkelstein B. Ballard F. Jaffe JM. J. Pharm. Sci. 1984; 73: 1599
- 4b LeVier RR. Chandler ML. Wendel SR. In The Biochemistry of Silicon and Related Problems . Bendz G. Lindqvist I. Plenum Press; New York and London: 1978: 473
- 5 Imrie CT. Henderson PA. Chem. Soc. Rev. 2007; 36: 2096
- 6a Lee M. Ko S. Chang S. J. Am. Chem. Soc. 2000; 122: 12011
- 6b Kikukawa Y. Kuroda Y. Ymamguchi K. Mizuno N. Angew. Chem. Int. Ed. 2012; 51: 2434
- 6c Shimizu K. Kubo T. Satsuma A. Chem. Eur. J. 2012; 18: 2226
- 6d Krüger A. Albrecht M. Chem. Eur. J. 2012; 18: 652
- 6e Sawama Y. Masuda M. Yasakawa N. Nakatani R. Nishimura S. Shibata K. Yamada T. Monguchi Y. Suzuka H. Takagi Y. Sajiki H. J. Org. Chem. 2016; 81: 4190
- 7a Lee Y. Seomoon D. Kim S. Han H. Chang S. Lee PH. J. Org. Chem. 2004; 69: 1741
- 7b Ison EA. Corbin RA. Abu-Omar MM. J. Am. Chem. Soc. 2005; 127: 11938
- 7c Matsuo T. Kawaguchi H. J. Am. Chem. Soc. 2006; 128: 12362
- 7d Mitsudome T. Arita S. Mori H. Mizugaki T. Jitsukawa K. Kaneda K. Angew. Chem. Int. Ed. 2008; 47: 7938
- 7e Chauhan BP. S. Sarkar A. Chauhan M. Roka A. Appl. Organomet. Chem. 2009; 23: 385
- 7f John J. Gravel E. Hagége A. Li H. Gacoin T. Doris E. Angew. Chem. Int. Ed. 2011; 50: 7533
- 8 Sridhar M. Ramanaiah BC. Narsaiah C. Swamy MK. Mahesh B. Reddy MK. K. Tetrahedron Lett. 2009; 50: 7166
- 9a Mitzel NW. Shier A. Beruda H. Schmidbaur H. Chem. Ber. 1992; 125: 1053
- 9b Harvey MC. Nebergall WH. Peake JS. J. Am. Chem. Soc. 1957; 79: 1437
- 10 Reagents were searched for commercial availability using the eMolecules database, and general supplier websites. The presence of available hydrido-chlorosilanes was investigated with a range of suppliers including: Sigma–Aldrich, Alfa–Aesar, Thermo–Fischer (includes multiple companies), Combi-Blocks, Oakwood Chemicals, Gelest Inc, Strem Inc, TCI chemicals, and Matrix Scientific.
- 11a Patzold U. Roewer G. Herzog U. J. Organomet. Chem. 1996; 508: 147
- 11b Binder J. Fisher RC. Flock M. Sammler H.-G. Torvisco A. Uhlig F. Phosphorus, Sulfur Silicon Relat. Elem. 2016; 191: 478
- 12a Hager R. Steigelmann O. Muller G. Schmidbaur H. Chem. Ber. 1989; 122: 2115
- 12b Schmidbaur H. Zech J. Rankin DW. H. Robertson HE. Chem. Ber. 1991; 124: 1953
- 13a Kunai A. Ohshita J. J. Organomet. Chem. 2003; 686: 3
- 13b Wang W. Tan Y. He Z. Zhang Z. J. Organomet. Chem. 2014; 769: 29
- 14 Hayashi K. Iyoda J. Shiihara I. J. Organomet. Chem. 1967; 10: 81
- 15 Uvarov VM. deVekki DA. Reshetilovskii VP. Skrortsov NK. Russ. J. Gen. Chem. 2010; 80: 35