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DOI: 10.1055/s-2008-1078588
Friedel-Crafts Alkylation of Nitrogen Heterocycles Using [Bmim][OTf] as a Catalyst and Reaction Medium
Publication History
Publication Date:
08 July 2008 (online)
In Table 2, entry 9, Table 3, entry 4, and Table 4,
entry 4, the product structures were incorrect; the correct
entries are shown below. In addition, the column headings in Table
3 for Nucleophile and Epoxide were inverted.
Table 2 [Bmim][OTf]-Promoted Alkylation of Indoles with Styrene Oxidea Entry Nucleophile Epoxide Product Time (h) Yield (%)b 9 24 10 a Reaction conditions: indole (1.2 mmol), epoxide (1 mmol), [bmim][OTf] (0.5 mL), stirred under nitrogen atmosphere at r.t. for an appropriate time. b Isolated yields. c Yield after fourth cycle.
Table 3 [Bmim][OTf]-Promoted Ring Opening of Various Aromatic Epoxides with Indolea Entry Epoxide Nucleophile Product Time (h) Yield (%)b 4 2.5 78 a Reaction conditions: indole (1.2 mmol), epoxide (1 mmol), [bmim][OTf] (0.5 mL), stirred under nitrogen atmosphere at r.t. for an appropriate time. b Isolated yields.
Table 4 [Bmim][OTf]-Promoted Alkylation of Pyrroles with Aromatic Epoxidesa Entry Nucleophile Epoxide Product Time (h) Yield (%)b 4 3.5 78 a Reaction conditions: pyrrole (1.2 mmol), epoxide (1 mmol), [bmim][OTf] (0.5 mL), stirred under nitrogen atmosphere at r.t. for an appropriate time. b Isolated yields.