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Regioselective synthesis of 3,5-Functionalization BODIPY Dyes via radical-triggered oxidative cross-coupling of two C–H bonds

吕帆  Qingbao Gong  焦莉娟  郝二宏  
【摘要】:Boron dipyrromethene(BODIPY) dyes~1 are now being widely applied in diverse research fields.~2 The growing success of these compounds is closely associated with their excellent spectroscopic and photophysical properties,and their rich functionalization chemistry.~3 Traditional functionalization of BODIPY dyes is generally achieved by de novo synthesis using suitably prefunctionalized pyrroles.Recently,elegant research progress has been made on the postfunctionalization of certain reactive BODIPY dyes,for example,by using halogen or thioether functionalized BODIPY fluorophores.~4 However,these postfunctionalization methods often require the use of unstable intermediates and/or a long synthetic route.To address these issues,very recently,radical reaction has been used as a mild and powerful method to regioselective functionalization of BODIPY dyes.5 Copper-catalyzed α-benzylation of BODIPYs via radical-triggered oxidative cross-coupling of two C–H bonds and highly regioselective α-acylation on BODIPY dyes via tandem cross-dehydrogenative coupling with in situ deprotection has been developed in our group.(Figure 1)

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