Synthesis of low-generation, aryl-/alkyl-type, nonpolar dendrons carrying protected hydroxyalkyl groups in the periphery

An efficient convergent synthesis of first- and second-generation aryl-/alkyl-type nonpolar dendrons via Suzuki cross-coupling is described. The dendrons carry either one or two benzyl-protected hydroxyalkyl. groups/terminus. Iododesilylation reactions of aryltrimethylsilanes with iodo chloride are used as a tool for the incorporation of iodo, an important functionality for transition-metal-catalyzed cross-coupling reactions. In the case of sensitive aromatics, the addition of some donor solvent like diethyl ether proved effective in suppressing side reactions through electrophilic aromatic iodination.