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Selective aromatic carbon–oxygen bond cleavage of trifluoromethoxyarenes: a trifluoromethoxy group as a convertible directing group

✍ Scribed by Akinori Iijima; Hideki Amii

Book ID: 104095711
Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 173 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.08.002

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✦ Synopsis

An efficient method for selective activation of aromatic C-O bonds in trifluoromethoxyarenes is developed. Upon treatment with a metallic sodium/chlorotrimethylsilane system, trifluoromethoxyarenes undergo reductive dealkoxylation to provide the corresponding arylsilanes. Also the synthetic applications of the present reactions combined with ortho-metallation are described.

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