A novel copper-catalyzed direct acylation of BODIPYs with aldehydes via C–H bond activation was developed, in which acyl radicals were formed from aldehydes in the presence of TBHP as radical initiator, and selectively reacted with BODIPYs at the α-positions. This radical oxidative dehydrogenative cross-coupling reaction showed excellent functional group tolerance, and both heteroaromatic and aliphatic aldehydes could be effectively reacted to BODIPYs. Comparing with those of the corresponding starting BODIPYs, those α-acylated BODIPYs showed red-shifted absorption and emission, as well as decreased both HOMO and LUMO energies due to the installation of electron-deficient carbonyl groups. Furthermore, the α-acylated BODIPY provided an efficient access to α-acylated dipyrrin by removal of the BF₂ protecting groups, which showed sensitive and selective “turn-on” fluorescence response toward Zn²⁺ ion in aqueous buffer solution and living cells.

开发了一种新型铜催化的 BODIPYs 与醛类通过 C-H 键活化的直接酰化反应，其中在 TBHP 作为自由基引发剂存在下由醛类形成酰基自由基，并在 α 位与 BODIPYs 选择性反应。这种自由基氧化脱氢交叉偶联反应显示出优异的官能团耐受性，杂芳族和脂肪族醛均可有效地与 BODIPY 反应。与相应的起始 BODIPY 相比，那些 α-酰化 BODIPY 显示出红移的吸收和发射，以及由于缺电子羰基的安装导致 HOMO 和 LUMO 能量降低。此外，α-酰化 BODIPY 通过去除 BF _{2提供了对 α-酰化联吡啶的有效途径}保护基团，它对水性缓冲溶液和活细胞中的Zn ²⁺离子表现出敏感和选择性的“开启”荧光反应。