TY - JOUR A1 - Blangetti, Marco A1 - Fleming, Patricia A1 - O'Shea, Donal F. T1 - Use of mixed Li/K metal TMP amide (LiNK chemistry) for the synthesis of [2.2]metacyclophanes JF - Beilstein Journal of Organic Chemistry PY - 2011/// VL - 7 SP - 1249 EP - 1254 SN - 1860-5397 DO - 10.3762/bjoc.7.145 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.7.145 KW - benzylic metalation KW - LiNK chemistry KW - [2.2]metacyclophane KW - oxidative coupling KW - planar chirality N2 - A new two-step general approach to [2.2]metacyclophane synthesis from substituted m-xylenes is described. The strategy employs a selective benzylic metalation and oxidative C–C bond formation for both synthetic operations. Regioselective benzylic metalation is achieved using the BuLi, KOt-Bu, TMP(H) (2,2,6,6-tetramethylpiperidine) combination (LiNK metalation conditions) and oxidative coupling with 1,2-dibromoethane. The synthetic ease of this approach compares favourably with previously reported methods and allows for ready access to potentially useful planar chiral derivatives. ER -