Liu Taifeng, Qi Chaoran, Zhou Qinghai, Dai Wenying, Lan Yuying, Xu Lanting, Ren Junxia, Pan Yangyang, Yang Lei, Ge Yongchao, Qu Yang-Kun, Li Wenhua, Li Hexing, Xiao Shengxiong
The Education Ministry Key Lab of Resource Chemistry, Joint International Research Laboratory of Resource Chemistry, Ministry of Education, Shanghai Key Laboratory of Rare Earth Functional Materials, College of Chemistry and Materials Science, Shanghai Normal University, Shanghai 200234, China.
Org Lett. 2022 Jan 21;24(2):472-477. doi: 10.1021/acs.orglett.1c03498. Epub 2021 Nov 19.
Divergent synthesis of four contorted aromatics containing pentagons, a heptagon, and/or an azulene from the same difluorenyl pentacenediene precursor were realized in one step. The subtle differences in molecular structure were confirmed by X-ray crystallography. The mechanisms for the control of different products, which involve a ring-expansion rearrangement, Scholl reactions, and/or Mallory cyclization were proposed on the basis of control experiments and DFT calculations. Such development adds good structure versatility and materials accessibility to the study of contorted aromatics.
通过一步反应实现了从同一二芴基并五苯二烯前体出发，发散合成四种含有五边形、七边形和/或薁环的扭曲芳烃。通过X射线晶体学确定了分子结构的细微差异。基于对照实验和密度泛函理论（DFT）计算，提出了控制不同产物的机制，其中涉及扩环重排、肖尔反应和/或马洛里环化反应。这种进展为扭曲芳烃的研究增加了良好的结构多样性和材料可及性。
