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Solution‐Phase Synthesis of First‐Generation Tetraester Dendritic Branches Involving Microwave and/or Ultrasonic Irradiation
Author(s) -
Wiesbrock Frank,
Patteux Claudine,
Olszewski Tomasz K.,
Blanrue Amélie,
Heropoulos Georgios A.,
Steele Barry R.,
MichaScrettas Maria,
Calogeropoulou Theodora
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800325
Subject(s) - chemistry , dendrimer , microwave , methanol , nucleophilic aromatic substitution , halogen , potassium carbonate , microwave irradiation , nucleophilic substitution , photochemistry , combinatorial chemistry , organic chemistry , physics , alkyl , quantum mechanics , catalysis
Trifunctionalized aromatic cores were selectively protected to obtain precursors for bidirectional dendritic unit growth through stepwise divergent syntheses. The synthesis of first‐generation dendrimer building blocks was performed by nucleophilic substitution of bromomethyl‐substituted aromatic cores with diethyl malonate anions in the presence of carbonate in halogen‐free solvents. The screening of the reaction parameters revealed the optimum conditions for small‐ and larger‐scale synthesis: these require microwave or ultrasonic irradiation to achieve yields around 70 % in reaction times as short as 15 min. As a result of the heterogeneity of the reaction mixtures, efficient stirring was important to suppress byproduct formation.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)