New preparation and synthetic reactions of 3,3,3-trifluoropropynyllithium, -borate and -stannane: Facile synthesis of trifluoromethylated allenes, arylacetylenes and enynes

Masaki Shimizu, Masahiro Higashi, Youhei Takeda, Masahito Murai, Guofang Jiang, Yuiga Asai, Yoshiaki Nakao, Eiji Shirakawa, Tamejiro Hiyama

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)921-945
Number of pages25
JournalFuture Medicinal Chemistry
Volume1
Issue number5
DOIs
Publication statusPublished - Aug 1 2009

ASJC Scopus subject areas

  • Molecular Medicine
  • Pharmacology
  • Drug Discovery

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