Electrochemical synthesis of dendritic diarylcarbenium ion pools
摘要:
Dendritic diarylcarbenium ion pools were synthesized by the low temperature electrochemical oxidation of the corresponding dendritic (diarylmethyl)trimethylsilanes, which were prepared by use of the iterative method consisting of electrochemical activation and Friedel Crafts type coupling. Time-course NMR studies revealed that thermal stability of dendritic diarylcarbenium ions depends both on the generation of the dendritic structure and on the para-substituents of the terminal phenyl groups. Dendritic diarylcarbenium ions up to the third generation exhibited high reactivity as a carbon electrophile. (C) 2011 Elsevier Ltd. All rights reserved.
Electrochemical synthesis of dendritic diarylcarbenium ion pools
摘要:
Dendritic diarylcarbenium ion pools were synthesized by the low temperature electrochemical oxidation of the corresponding dendritic (diarylmethyl)trimethylsilanes, which were prepared by use of the iterative method consisting of electrochemical activation and Friedel Crafts type coupling. Time-course NMR studies revealed that thermal stability of dendritic diarylcarbenium ions depends both on the generation of the dendritic structure and on the para-substituents of the terminal phenyl groups. Dendritic diarylcarbenium ions up to the third generation exhibited high reactivity as a carbon electrophile. (C) 2011 Elsevier Ltd. All rights reserved.
Iterative Molecular Assembly Based on the Cation-Pool Method. Convergent Synthesis of Dendritic Molecules
作者:Toshiki Nokami、Kousuke Ohata、Masafumi Inoue、Hiroaki Tsuyama、Akito Shibuya、Kazuya Soga、Masayuki Okajima、Seiji Suga、Jun-ichi Yoshida
DOI:10.1021/ja803487q
日期:2008.8.1
An iterative method for molecular assembly has been developed based on the cation-pool methodusing (trimethylsilyl)diphenylmethane as a building block. The silyl group works as both an activating group of the benzene ring in the Friedel-Crafts type reaction and an electroauxiliary in the subsequent low temperature anodic oxidation to generate dendritic diarylcarbenium ions, which were well characterized