3 years ago

Efficient Modular Synthesis of Substituted Borazaronaphthalene

Efficient Modular Synthesis of Substituted Borazaronaphthalene
Jing-Hui Yang, Jie-Yu Wang, Qi-Ran Chen, Sheng Tang, Fang-Dong Zhuang, Jian Pei, Ji-Min Han
A highly efficient modular synthetic method for BN-fused polycyclic aromatic hydrocarbons (PAHs) composed of a borazaronaphthalene core along with multiple functionalized sites is reported. The halogenated 2,1-borazaronaphthalene cores are constructed through a ring-closing reaction between o-ethynylaniline derivatives and boron halides. The controllable halogen substituents make further derivatization of 2,1-borazaronaphthalene cores feasible by using metal-catalyzed cross-coupling reactions. On the basis of the carefully designed precursors, various functional aromatic rings can be fused to the azaborine core via a one-pot nucleophilic tandem reaction, affording previously inaccessible PAHs in moderate yields.

Publisher URL: http://dx.doi.org/10.1021/acs.organomet.6b00811

DOI: 10.1021/acs.organomet.6b00811

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