Platinum-catalyzed aromatic C-H silylation of arenes with 1,1,1,3,5,5,5-heptamethyltrisiloxane

Chemistry Letters

Volumn 36, Issue 7, 2007, Pages 910-911

  Murata, Miki ^a   Fukuyama, Naoaki ^a   Wada, Jun Ichi ^a   Watanabe, Shinji ^a   Masuda, Yuzuru ^a  

^a KITAMI INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34547155516     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2007.910     Document Type: Article

References (21)

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15. Quite recently, Miyaura et al. reported on an iridium-catalyzed C-H silylation using 1-hydrosilatrane. See: E. Kishida, T. Saiki, T. Ishiyama, N. Miyaura, 53rd Symposium on Organometallic Chemistry, Osaka, Japan, September, 2006, Abstr. No., PB253;
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19. 1,1,1,3,5,5,5-Heptamemyltrisiloxane (1) is commercially available.
20. Me2K (15 μmol) were placed in a resealable Schlenk tube. The tube was evacuated and backfilled with nitrogen and then charged with the arene 2 (5 mmol). After being stirred at room temperature for 1 h, 1,1,1,3,5,5,5-heptamethyltrisiloxane (1; 0.50 mmol) was added. The reaction mixture was then stirred at 200°C for 24 h. After the reaction, the mixture was analyzed by GC and GC-MS. The volatile material was removed in vacuo, and the residue was purified by Kugelrohr distillation to afford the desired 3-aryl-1,1,1,3,5,5,5-heptamethyltrisiloxane 3.
21. Relative product ratios from the reactions in equimolar mixtures of benzene (2a) and substituted arenes 2b, 2c, and 2e were 1:1.33, 1:0.61, and 1:0.40, respectively.