Regioselective and Stepwise Syntheses of Functionalized BODIPY Dyes through Palladium-Catalyzed Cross-Coupling Reactions and Direct C–H Arylations

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• 作者：Zeya Feng ; Lijuan Jiao ; Yuanmei Feng ; Changjiang Yu ; Na Chen ; Yun Wei ; Xiaolong Mu ; Erhong Hao
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：August 5, 2016
• 年：2016
• 卷：81
• 期：15
• 页码：6281-6291
• 全文大小：771K
• 年卷期：0
• ISSN：1520-6904

文摘

Regioselective and stepwise syntheses of a series of functionalized BODIPY dyes through palladium-catalyzed cross-coupling reactions and direct C–H arylations have been developed. In particular, this method allows the straightforward synthesis of 2,6-dibromo-3,5-diarylBODIPYs and 2-bromo-3-arylBODIPYs from polybrominated BODIPYs. The X-ray structure of intermediates 5a–c indicated that the palladium was first inserted into the C–Br bonds at 3,5-positions of brominated BODIPYs. The resulting 2,6-dibromo-substituted BODIPYs are potential long wavelength photosensitizers which are not easily accessible using previous methods.