有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
総説および総合論文
芳香族フッ化物の脱フッ素ホウ素化反応
丹羽 節細谷 孝充
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2019 年 77 巻 9 号 p. 883-894

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Fluoroarenes are widely found in molecules involving pharmaceuticals, agrochemicals, and organic functional materials. The fluoro group is often installed to the molecules to provide favorable characteristics that rest on unique properties of fluorine. The increasing availability of fluoroarenes has stimulated considerable interest in their late-stage transformation via C-F bond cleavage, which is a challenging issue to achieve due to high stability of the C-F bond. Particularly, defluoroborylation of fluoroarenes has been attracting much attention owing to the reliable and versatile organoboron chemistries that enable facile diversification for obtaining valuable compounds such as drug candidates and molecular probes that promote researches in drug discovery and life science. In this article is reviewed the recent progress made on this challenging issue. These include borylation of perfluoroarenes having a fluoro group with relatively high leaving ability, low-valent transition metal-catalyzed defluoroborylation of fluoroarenes bearing an inert C-F bond, and promising photochemical defluoroborylation of fluoroarenes.

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