Regioselective C₃Alkylation of Indoles for the Synthesis of Bis(indolyl)methanes and 3-Styryl Indoles

Herein, we describe an efficient transition-metal-free regioselective C(3)alkylation of indoles for the synthesis of bis-(indolyl)-methanes and 3-styryl indoles. Nitrobenzene is employed as the oxidant to oxidize the alcohols in the presence of a strong base and the reaction avoids the use of transition metals such as Ru and Mn. The protocol provides a favorable route to access biologically active compounds such as arundine, vibrindole A, and turbomycin B.