In this work, a metal-free, regioselective, formal coupling reaction between C(sp2) of indoles and the C(sp3) of benzo[c]oxepines has been realized. This method provides an efficient approach for the synthesis of 3-(2-methylbenzyl)indole derivatives. Based on the experimental results, a sequential ring-opening/[1,5]H-shift/Michael addition mechanism was proposed. ©...