1,3-Diaryl propargyl alcohols undergo smooth intramolecular Friedel-Crafts cyclization with triethylsilane in the presence of 10 mol % iodine 3-aryl-1H-indene derivatives in good yields in short reaction times. This is the first example on the synthesis of substituted indenes from 1,3-diaryl propargyl alcohols. The use of inexpensive and readily available molecular iodine makes this method quite simple, more convenient, and practical. (C) 2010 Elsevier Ltd. All rights reserved.
Synthesis of indenes via aluminum chloride-promoted tandem Friedel–Crafts alkylation of arenes and cinnamaldehydes
作者:Haiouani Kheira、Pingfan Li、Jiaxi Xu
DOI:10.1016/j.molcata.2014.04.027
日期:2014.9
A series of substituted indenes were synthesized from arenes and cinnamaldehydes via aluminum chloride-promoted tandem Friedel-Crafts alkylation. The scope and limitation of the tandem reaction were explored. A plausible reaction mechanism is also discussed. This approach provides a convenient method for the synthesis of indene derivatives using a readily available and low cost Lewis acid and starting materials. (C) 2014 Elsevier B.V. All rights reserved.