Abstract
An efficient and convenient method was developed for the one-step synthesis of various substituted ethyl 2-(1H-indol-2-yl) acetates via a palladium-catalyzed regioselective cascade C-H activation reaction. Importantly, this practical approach can be carried out with readily accessible starting materials and exhibits excellent functional group compatibility.
Highlights
An efficient and convenient method was developed for the one-step synthesis of various substituted ethyl 2-(1H-indol-2-yl) acetates via a palladium-catalyzed regioselective cascade C-H activation reaction
As part of our continuing effort to assemble indole-based drug scaffolds [59,60,61], we here present our findings on one-step synthesis of various substituted ethyl 2-(1H-indol-2-yl)acetates via a palladium-catalyzed regioselective cascade C-H activation reaction
The higher water content in the solvents was found to significantly increase the selectivity for the mono-2-substituedindole product 1 (Table 1), but led to a compromised conversion rate. These results suggest that water might serve as the hydrogen source in the catalytic system, which accelerates the norbornene-mediated cascade reaction by hydrolysing the final arylpalladium(II) species
Summary
An efficient and convenient method was developed for the one-step synthesis of various substituted ethyl 2-(1H-indol-2-yl) acetates via a palladium-catalyzed regioselective cascade C-H activation reaction. As part of our continuing effort to assemble indole-based drug scaffolds [59,60,61], we here present our findings on one-step synthesis of various substituted ethyl 2-(1H-indol-2-yl)acetates via a palladium-catalyzed regioselective cascade C-H activation reaction. The direct application of the reported optimized reaction conditions yielded diethyl 2,2’-(1H-indole-2,3-diyl) diacetate, a 2,3-disubstitued-indole product, as the major product.
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