Boron-Masking Strategy in Iterative Suzuki-Miyaura Coupling for Selective Synthesis of Oligoarenes

摘要

The Suzuki-Miyaura reaction is recognized as one of the most reliable and convenient methods for the aryl-aryl coupling, using arylboronic acid with aryl halides or pseudo halides. On the of the high versatility of the coupling, it is eagerly desired to develop the general method for the selective synthesis of oligoarenes, which are expected as new functional materials, In this paper, we disclose new boron-masking strategy for the iterative cross-coupling reaction, using 1,8-diaminonaphthalene as an efficient masking group. The strategy involves coupling of masked halo-substituted arylboronic acids with organoboronic acids,leading to selective formation of biarylboronic acids, of which the masking group is retained.