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

Communication

JOURNAL 3516

Organic Communications

VOLUME & ISSUE

Year: 2025 Issue: 3 July-September

PAGES

p.200 - 207

DOI ADDRESS

http://doi.org/10.25135/acg.oc.192.2505.3516

STATISTICS

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AUTHORS

Yogesh Jorapur
Gurusamy Rajagopal
Rajendra Kankariya

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 A6-192-OC-2505-3516-SI.pdf (450.64 KB)