The Bis(indolylmethyl) ethers: Design, Prototypical Synthesis, and Scope Studies.

The design, prototypical synthesis, isolation, and characterization of bis(indolylmethyl) ethers from corresponding indolylcarbinols is described. This approach involves very mild conditions and exhibits good scope for indolylcarbinols (both N -electron withdrawing group and N -electron donating group). Cross etherification between two electronically different indolylcarbinols is also demonstrated for the generation of unsymmetrical ethers. For the first time, the intermediacy of the bis(indolylmethyl) ethers for the formation of bis(indolyl)methanes from indolylcarbinols is proved experimentally and by 1 H NMR analysis.