Abstract
Within this contribution, the development and substrate scope evaluation of a direct alkylation protocol of the C(sp3)–H bond of benzylic amines using alkyl bromides is reported. This pyridine-directed method is initiated by elimination of the alkyl bromide to a terminal olefin, which is then the true alkylating agent.Graphical abstract
Highlights
Direct C–H functionalization via metal catalysis is emerging as one of the most frequently investigated methods in recent years
The largest part of research is dedicated to functional group directed C–H functionalization reactions
All of the most frequently occurring functional groups have been used as a directing group, at least in a small set of examples [5, 6]
Summary
Direct C–H functionalization via metal catalysis is emerging as one of the most frequently investigated methods in recent years. 3‐Methyl‐N‐(1‐phenylpropyl)pyridin‐2‐amine (2) The reaction was carried out according to general procedure A with 100 mg 1 (0.50 mmol, 1 eq.), 163 mg 1-bromoethane (1.50 mmol, 3 eq.), 311 mg K2CO3 (2.25 mmol, 4.5 eq.), and 12 mg [RhCl(cod)]2 (0.025 mmol, 0.05 eq.) in 2 cm3 dry and degassed toluene.
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