Abstract
A rhodium-catalyzed alkylation reaction of indoles with N-Boc-imines has been developed via C-H activation to afford a series of substituted 2-indolyl-methanamine derivatives with good functional group tolerance and regioselectivity. A wide range of indole-based alkylation products could be obtained in up to 95% yield.
Highlights
Transition-metal-catalyzed aromatic C−H functionali zation has been recognized to be a highly important synthetic tool for its atom-economical routes to functionalized aromatic molecules.[1]
RhIII catalytic C−H bond activation is an attractive strategy for preparing amino-containing aromatic compounds which are commonly found in pharmaceuticals as well as natural products and functional materials.[3]
Strong solvent effects have been observed, such as the reaction proceeded well in 1,2-dichloroethane (DCE) and dichloromethane (DCM), whereas toluene (PhMe) and tert‐butyl alcohol (t-BuOH) were not suitable for this reaction, in which we could not observe the full conversion of starting materials despite prolonging the reaction time to 24 h (Table 1, entries 6-8)
Summary
Transition-metal-catalyzed aromatic C−H functionali zation has been recognized to be a highly important synthetic tool for its atom-economical routes to functionalized aromatic molecules.[1]. Zhou et al.[10] successfully reported a RhIII-catalyzed regioselective addition of indole C−H bonds to aryl- and alkyl-N-sulfonylimines for the preparation of 2-indolyl-methanamine derivatives with good functional group tolerance, but in relatively low yields (between 42 to 71%, see Scheme 1).
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