Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 8, Issue 4, Pages 482-486Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201900152
Keywords
tandem reactions; iodine; C-H activation; aza-Michael addition; indoles
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Funding
- National Natural Science Foundation of China [21571121, 21771122, 21602129]
- 111 Project [B14041]
- Program for Changjiang Scholars and Innovative Research Team in University [IRT_14R33]
- Natural Science Basic Research Plan in Shaanxi Province of China [2017JM2020]
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An efficient iodine-mediated aza-Michael addition/C-H functionalization procedure for the synthesis of indoles was achieved in one pot. By simple aza-Michael addition between anilines and alpha,beta-ynones, a series of N-aryl enaminones intermediate was generated, followed by iodine-mediated C-H functionalization, a wide variety of indole derivatives were obtained in moderate to excellent yields under transition-metal-free conditions. Control experiments and insitu ESI-MS analysis indicated the reaction occurred via a radical mechanism.
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