We present a new
acid-free method for the generation of carbocations
based on a redox condensation reaction that enables SN1
reactions with a variety of nucleophiles. We utilize readily synthesized
phosphinites that are activated by diisopropyl azodicarboxylate to
form betaine structures that collapse upon adding a pronucleophile,
thereby yielding reactive carbocation intermediates. We also employ
this approach for the alkylation of some bioactive molecules.
The synthesis of [n]cycloparaphenylenes ([n]CPPs) and similar nanohoops is usually based on the combination of building blocks to a macrocyclic precursor, which is then aromatized in the final step. Access to those building blocks in large amounts will simplify the synthesis and studies of CPPs as novel functional materials in applications. Herein, we report a continuous flow synthesis of key CPP building blocks using versatile synthesis techniques such as electrochemical oxidation, lithiations and Suzuki cross couplings in self‐built reactors on up‐to kilogram scale.
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