2009年8月
New preparation and synthetic reactions of 3,3,3-trifluoropropynyllithium, -borate and -stannane: facile synthesis of trifluoromethylated allenes, arylacetylenes and enynes
FUTURE MEDICINAL CHEMISTRY
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- 巻
- 1
- 号
- 5
- 開始ページ
- 921
- 終了ページ
- 945
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.4155/fmc.09.69
- 出版者・発行元
- FUTURE SCI LTD
Background: Since trifluoromethyl-containing compounds have found diverse applications in the fields of pharmaceuticals and agrochemicals, facile and selective synthetic methods for trifluoromethyl-substituted compounds are an essential tool for advanced medicinal chemistry. Now that diverse synthetic transformations of carbon carbon triple bonds are available, 3,3,3-trifluoropropynyl-substituted compounds serve as versatile building blocks for target molecules containing trifluoromethyl groups. Thus, novel synthetic methods and reagents for incorporation of a 3,3,3-trifluoropropynyl group into an organic compound have been the major concern in exploration and modification of fluorine-based biologically active substances. Results & discussion: We report a preparative method of 3,3,3-trifluoropropynyllithium and its reaction with electrophiles including aldehydes, ketones, trimethoxyborane, chlorosilanes and chlorostannanes in detail. Palladium-catalyzed synthetic reactions of the carbonyl adducts and the trifluoromethyl-containing metalloid reagents are also demonstrated, which provide simple synthetic methods of trifluoromethylated allenes, arylacetylenes and enynes. The synthetic transformations presented here expand the repertoire of trifluoromethylated compounds available for medicinal scientists and contribute to the advance of future medicinal chemistry.
- リンク情報
- ID情報
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- DOI : 10.4155/fmc.09.69
- ISSN : 1756-8919
- eISSN : 1756-8927
- PubMed ID : 21426090
- Web of Science ID : WOS:000276093600017