Regioselective pyrrole C–benzylation using hexaethylene glycolic ionic liquids as a recyclable catalyst

Short Communication

JOURNAL 3516

Organic Communications
VOLUME & ISSUE
Available Online: July 28,2025
PAGES
p.1 - 8
DOI ADDRESS
http://doi.org/10.25135/acg.oc.192.2505.3516
(DOI number will be activated after the manuscript has been available in an issue.)
STATISTICS
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AUTHORS
  • Yogesh Jorapur
  • Gurusamy Rajagopal
  • Rajendra Kankariya
PDF OF ARTICLE

GRAPHICAL ABSTRACT

ABSTRACT

We have thoroughly investigated the C-benzylation of pyrrole (1) using different second and third generation ionic liquids (ILs). The pyrrole C-benzylation is achieved with benzyl halides, mesylate, and tosylate selectively at C2 position in good yield. Moreover, minimal byproducts under relatively mild conditions in hexaethylene glycol substituted imidazolium based ILs (hexaEGILs) have been observed. 2-Benzyl pyrrole (3) was synthesized in high yield from pyrrole (1) and benzyl bromide (2a) in the presence of [hexaEGmim][OMs] and [dihexaEGim][OMs] as two different tailor-made ILs as catalysts (10 mol%) in MeCN at 80 oC within an hour.

 KEYWORDS
  • Pyrrole benzylation
  • benzyl bromide
  • ionic liquids
  • ethylene glycols
  • green chemistry

SUPPORTING INFORMATION

Supporting Information
Download File 192-OC-2505-3516-SI.pdf (1.53 MB)