Synthesis 2016; 48(20): 3559-3566
DOI: 10.1055/s-0035-1561655
paper
© Georg Thieme Verlag Stuttgart · New York

Ionic Liquid [DABCO-H][HSO4] as a Highly Efficient and Recyclable Catalyst for Friedel–Crafts Alkylation in the Synthesis of Bis(naphthol)methane and Bis(indolyl)methane Derivatives

Jun Tong
National Pesticide Engineering Research Center (Tianjin), State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: xudazhen@nankai.edu.cn
,
Cheng Yang
National Pesticide Engineering Research Center (Tianjin), State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: xudazhen@nankai.edu.cn
,
Da-zhen Xu*
National Pesticide Engineering Research Center (Tianjin), State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: xudazhen@nankai.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 07 March 2016

Accepted after revision: 29 April 2016

Publication Date:
13 June 2016 (online)


Abstract

A simple and highly efficient approach to the synthesis of bis(naphthol)methane (BNM) and bis(indolyl)methane (BIM) derivatives has been developed. In the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO)-based ionic liquid catalysts, which are environmental friendly, inexpensive, and recyclable, the reaction afforded the corresponding products in good to excellent yields within short times under solvent-free conditions. The catalysts can be easily recovered and reused several times without significant loss in activity.

Supporting Information