Mixed Alkylamido Aluminate As A Kinetically Controlled Base

摘要

The mechanisms by which directed ortho metalation (DoM) and postmetalation processes occur when aromatic compounds are treated with mixed alkylamido aluminate i-Bu_3AI(TMP)Li (TMP-aluminate 1; TMP = 2,2,6,6-tetramethylpiperidide) have been investigated by computation and X-ray diffraction. Sequential reaction of ArC(=O)N(i-Pr)_2 (Ar = phenyl, 1-naphthyl) with t-BuLi and i -Bu_3AI in tetrahydrofuran affords [2-(i-Bu_3AI)C_mH_nC(=O)N(i-Pr)_2]Li·3THF (m = 6, n = 4, 7; m = 10, n = 6, 8).