Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 1, Pages 23-26Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b10061
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Funding
- MEXT (Strategic Promotion of Innovative Research, JST)
- MEXT [15H05754]
- Grants-in-Aid for Scientific Research [16H01005, 26708011, 15H05754] Funding Source: KAKEN
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Upon zincation of two acidic protons attached to the nitrogen and the sp-carbon atoms, a N-protected 2-ethynylaniline cyclizes to a 2,3-dizincioindole at 120 degrees C. Driven by the energy gain due to formation of two C-Zn bonds, this reaction occurs smoothly without side reactions, although this transformation is intrinsically endothermic in its bare anionic form. The resulting dizinc intermediate can be functionalized with one or two different electrophiles either inter- or intramolecularly on either C-2 or C-3 selectively, depending on the choice of catalyst and the electrophiles. This conversion of 2ethynylaniline to 2,3-dimetalloindole can be applied to an expeditious synthesis of indenoindolone and benzodipyrrole derivatives, which are compounds of interest for medicinal chemistry and materials science, respectively.
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