Organic Letters
Organic Letters
5 years ago

Dual Activation of Nucleophiles and Electrophiles by N-Heterocyclic Carbene Organocatalysis: Chemoselective N-Imination of Indoles with Isocyanides

Dual Activation of Nucleophiles and Electrophiles by N-Heterocyclic Carbene Organocatalysis: Chemoselective N-Imination of Indoles with Isocyanides
Jungwon Kim, Soon Hyeok Hong
The first chemoselective N-imination of indoles with isocyanides by using an N-heterocyclic carbene (NHC) as an organocatalyst was achieved. A concurrent activation of nucleophile (indole) and electrophile (isocyanide) took place facilitated by the novel NHC organocatalysis via initial activation of isocyanide. The in situ generated indole anion and imine-azolium species performed a coupling reaction, producing several new indole-based formamidines in high yields under mild conditions, which was not feasible via previously reported strategies.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01377

DOI: 10.1021/acs.orglett.7b01377

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