Oxidation of gem-borylsilylalkylcoppers to acylsilanes with air

Organic Letters

Volumn 8, Issue 6, 2006, Pages 1185-1187

  Kondo, Junichi ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

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Indexed keywords

EID: 33646440600     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0600988     Document Type: Article

References (18)

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9. For reviews on the synthesis and utility of acylsilanes, see: (a) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647.
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13. Dichloromethylsilanes 1a-c are easily prepared according to the reported procedure. (a) Bacquet, C.; Masure, D.; Normant, J. F. Bull. Soc. Chim. Fr. 1975, 1797.
14. (b) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron 1996, 52, 503.
15. Hiyama et al. previously reported the synthesis of 2b through gem-dimetalation of lithium carbenoids with silylboranes. See: Shimizu, M.; Kurahashi, T.; Kitagawa, H.; Shimono, K.; Hiyama, T. J. Organomet. Chem. 2003, 686, 286.
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18. Silanol 8a may result from competing migration of the silyl group. However, we could detect neither the presumed product, acylborane from β-elimination of silyl group, nor its hydrolyzed products.