Mechanochemical Metal-Free Synthesis of 3-Arylindenones via Unprecedented Aryl Swapping  

作　　者：Liang Li Chuang Niu Guan-Wu Wang 

机构地区：[1]Hefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry,University of Science and Technologyof China,Hefei,Anhui230026,China [2]Department of Chemistry and Chemical Engineering,Hefei Normal University,Hefei,Anhui 230601,China

出　　处：《Chinese Journal of Chemistry》2022年第21期2539-2545,共7页中国化学（英文版）

基　　金：support from the National Natural Science Foundation of China(No.21372211);the High-Level Scientific Research Foundation for the Introduction of Talent of Hefei Normal University(2020rcj31);theNatural Science Foundation of the Education Department of Anhui Province(KJ2019A0733).

摘　　要：A triflic anhydride-induced annulation of benzoic acids bearing electron-withdrawing groups with arylalkynes leading to diverse 3-arylindenones via an unprecedented aryl swapping pathway under an air atmosphere and ball-milling conditions has been disclosed.Most of the obtained 3-arylindenones are fluorine-containing compounds.The present mechanochemical protocol employs easily available and inexpensive benzoic acids,which unexpectedly undergo aryl swapping with arylalkynes and serve as the source of the 3-aryl group.The current mechanochemical methodology shows advantages including no requirement of transition-metal catalysts,ambient conditions and excellent regioselectivity for the rearrangement products,providing expedient access to 3-arylindenones containing functional groups such as F,Cl,Br,CF3,OCF3,SCF3,OAc,Ac,CO_(2)Et or NO_(2).

关 键 词：MECHANOCHEMISTRY REARRANGEMENT 3-Arylindenones Carboxylic acids ALKYNES Green chemistry 

分 类 号：O62[理学—有机化学]