Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 19, Issue -, Pages 1379-1385Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.19.99
Keywords
alkynylation; catalysis; cyclization; indoles; iodination; multicomponent reactions
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A library of 19 differently substituted 3-iodoindoles has been generated by a consecutive four-component reaction, which provides a concise one-pot synthesis of valuable substrates for Suzuki arylations. Some of the synthesized compounds exhibit good reaction activity and emission properties in the Suzuki arylations.
A library of 19 differently substituted 3-iodoindoles is generated by a consecutive four-component reaction starting from ortho- haloanilines, terminal alkynes, N-iodosuccinimide, and alkyl halides in yields of 11-69%. Initiated by a copper-free alkynylation, followed by a base-catalyzed cyclizive indole formation, electrophilic iodination, and finally electrophilic trapping of the intermediary indole anion with alkyl halides provides a concise one-pot synthesis of 3-iodoindoles. The latter are valuable substrates for Suzuki arylations, which are exemplified with the syntheses of four derivatives, some of them are blue emitters in solution and in the solid state, in good yield.
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