Affiliation:
1. Key Laboratory of Chemical Biology and Traditional Chinese Medicine Ministry of Educational of China Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province College of Chemistry and Chemical Engineering Hunan Normal University Changsha 410081 China
Abstract
AbstractCarbazole‐incorporated smaragdyrin BF2‐complex 3 was synthesized by SNAr reaction of 3,5‐dibromo‐8‐mesityl‐BODIPY 1 with 3,6‐di(tert‐butyl)‐1,8‐di(pyrrol‐2‐yl)carbazole 2 as a nucleophile. Demetalation of 3 with ZrCl4 gave the corresponding smaragdyrin free base 4 in a good yield. Oxidations of 3 and 4 with MnO2 gave smaragdyrins 5 and 6, respectively, both followed by aromaticity switching, since the oxidized products showed a moderate paratropic ring current owing to their 20π‐electronic circuits. Further, treatment of 4 with [RhCl(CO)2]2 in the presence of NaOAc gave RhI complex 7, and oxidation of 3 with RuCl3 in the presence of triethylamine led to the formation of a spiro dimer product, 8.
Funder
National Natural Science Foundation of China