Journal
JOURNAL OF FLOW CHEMISTRY
Volume 6, Issue 2, Pages 117-122Publisher
AKADEMIAI KIADO RT
DOI: 10.1556/1846.2015.00030
Keywords
flow chemistry; C-H activation; catalytic alkylation; nickel catalysis
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Funding
- European Community [CP-IP 246095]
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A novel method for C-H functionalization of heteroaromatic rings by using continuous-flow reactors is reported. Direct alkylation reactions were investigated under heterogeneous catalytic conditions using simple transition metal catalysts at elevated temperature and pressure. As a model reaction, the alkylation of indole was attempted using cheap Raney (R) Nickel catalyst. Alcohols served both as alkylating agent and as reaction media. The targeted 3-alkyl-indoles were obtained in moderate to good yield with reasonable selectivity. Transient protection on the N-atom increased the selectivity up to 80%. The scope and limitations were also investigated. In summary, direct alkylation with alcohols represents a rapid (residence time of <1 min) and traceless process with high atom economy (88-92%, in those cases where transient protection was not applied).
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