Aiming to shed new light on the stability and constitution of the organometallic intermediates involved in direct ortho-metalation processes, using trifluoromethylbenzene (1) as a case study, this paper investigates the deprotonation of 1 using group 1 alkyl bases t BuLi and n BuNa in the presence of the Lewis donors TMEDA (N, N, N′, N′- tetramethylethylenediamine), THF, and PMDETA (N, N, N′, N ″, N ″- ...