García-Santos William H, Ordóñez-Hernández Javier, Farfán-Paredes Mónica, Castro-Cruz Hiram M, Macías-Ruvalcaba Norma A, Farfán Norberto, Cordero-Vargas Alejandro
Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior s/n, Ciudad Universitaria, Coyoacán, C.P., México, D.F. 04510, México.
Facultad de Química, Departamento de Química Orgánica, Universidad Nacional Autónoma de México, Ciudad de México 04510, México.
J Org Chem. 2021 Dec 3;86(23):16315-16326. doi: 10.1021/acs.joc.1c01598. Epub 2021 Nov 2.
A new dibrominated 4,4-difluoro-4-bora-3a,4a-diaza--indacene (BODIPY) is reported as a new metal-free photocatalyst. This BODIPY showed similar optoelectronic, electrochemical, and performance properties to those of Ru(bpy)Cl, one of the most common photocatalysts in a known radical-ionic transformation, such as the formation of 1,4-dicarbonyl compounds. Moreover, additional sequences in which the generated oxonium ion is trapped by an internal nucleophile were developed using this BODIPY photocatalyst. These new sequences allowed the straightforward preparation of γ-alkoxylactones, monoprotected 1,4-ketoaldehydes, and dihydrofurans. This new catalyst, the methodology, and the forged functional groups could be important tools in organic synthesis.
据报道，一种新型的二溴化4,4-二氟-4-硼-3a,4a-二氮杂茚（BODIPY）是一种新型无金属光催化剂。这种BODIPY在光电子、电化学和性能方面表现出与Ru(bpy)Cl相似的性质，Ru(bpy)Cl是已知自由基离子转化中最常用的光催化剂之一，例如1,4-二羰基化合物的形成。此外，利用这种BODIPY光催化剂开发了额外的反应序列，其中生成的氧鎓离子被内部亲核试剂捕获。这些新的反应序列使得γ-烷氧基内酯、单保护的1,4-酮醛和二氢呋喃的直接制备成为可能。这种新型催化剂、方法以及所形成的官能团可能成为有机合成中的重要工具。
