Iterative Molecular Assembly Based on the Cation-Pool Method. Convergent Synthesis of Dendritic Molecules

• Published in: Journal of the American Chemical Society Vol. 130; no. 33; pp. 10864 - 10865
• Main Authors: Nokami, Toshiki, Ohata, Kousuke, Inoue, Masafumi, Tsuyama, Hiroaki, Shibuya, Akito, Soga, Kazuya, Okajima, Masayuki, Suga, Seiji, Yoshida, Jun-ichi
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 20.08.2008; Amer Chemical Soc
• Subjects: Benzhydryl Compounds - chemistry; Cations - chemistry; Chemistry; Chemistry, Multidisciplinary; Dendrimers - chemical synthesis; Dendrimers - chemistry; Molecular Structure; Physical Sciences; Science & Technology; Stereoisomerism; OXIDATION; STATES; REDUCTION; CHEMISTRY; IONS; ORGANOSILICON; GENERATION; DENDRIMERS; CARBON-SILICON BOND; BENZYLSILANES
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja803487q

An iterative method for molecular assembly has been developed based on the cation-pool method using (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 by low-temperature NMR spectroscopy. The convergent synthesis of dendritic molecules has been achieved by repeating the sequence.