Divergent Synthesis of Chiral Covalent Organic Frameworks

作者：Li‐Ke Wang, Jingjing Zhou, Yu‐Bao Lan, San‐Yuan Ding, Wei Yu, Wei Wang · 发表于：Angewandte Chemie International Edition · 年份：2019 · DOI：10.1002/anie.201903534 · 被引用次数：136 · 研究领域：Covalent Organic Framework Applications、Metal-Organic Frameworks: Synthesis and Applications、Supramolecular Chemistry and Complexes

Featuring the simultaneous generation of a library of compounds from a certain intermediate, divergent synthesis has found increasing applications in the construction of natural products and potential medicines. Inspired by this approach, presented herein is a general strategy to introduce functionality, in a divergent manner, into covalent organic frameworks (COFs). This modular protocol includes two stages of covalent assembly, through which functional COFs can be constructed by a three-step transformation of a key platform molecule, such as 4,7-dibromo-2-chloro-1H-benzo[d]imidazole (DBCBI). Constructed herein are four types of chiral COFs (CCOFs) from DBCBI by nucleophilic substitution, Suzuki coupling, and imine formation. The unique array of eight isoframework CCOFs allowed investigation of their catalytic performance and structure-activity relationship in an asymmetric amination reaction.