Journal
ORGANIC LETTERS
Volume 22, Issue 1, Pages 140-144Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b04060
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Funding
- National Natural Science Foundation of China [21971080, 21971079, 21602070, 21772051, 21877046]
- Fundamental Research Funds for the Central Universities [CCNU15ZX002, CCNU18QN011]
- 111 Project [B17019]
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We report an I-2/FeCl3-co-promoted formal [2 + 2+1] annulation of aryl methyl ketones, 2-aminobenzyl alcohols, and p-toluenesulfonylmethyl isocyanide (TosMIC) by neighboring group (-CH2OH) assistance. This is a novel example of using the Van Leusen reagent as a unique C1N1 two-atom synthon in the synthesis of imidazoles. Preliminary mechanism studies showed that TsCH2NH2 might be the key intermediate in this reaction. Furthermore, this reaction not only unlocks a novel strategy for imidazole synthesis, but also exploits a new reactivity of TosMIC.
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