Organic Letters
Organic Letters
5 years ago

Metal-Free Multiple Carbon–Carbon and Carbon–Hydrogen Bond Activations via Charge-Switching Mechanism in Unstrained Diindolylmethanes

Metal-Free Multiple Carbon–Carbon and Carbon–Hydrogen Bond Activations via Charge-Switching Mechanism in Unstrained Diindolylmethanes
Ravi S. Lankalapalli, Cherumuttathu H. Suresh, Sunil Varughese, Chandrasekhar Challa
A transformation of the unstrained phenol substituted 3,3′-diindolylmethanes (DIPMs) to 2,3′-diindolylketones (DIKs) by double C–C single bond cleavage with associated rearrangements, triggered by phenyliodine(III) diacetate (PIDA), is reported. Density functional theory studies reveal a mechanism involving multiple “charge-switching” steps by synergistic involvement of the two indole units with overall low activation energy. The indole ‘charge-switching’ mechanism in DIPMs was further extended toward synthesis of a natural product motif cyclohepta[b]indole from biaryl appended DIBM.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01843

DOI: 10.1021/acs.orglett.7b01843

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