Gilman-Type versus Lipshutz-Type Reagents: Competition in Lithiocuprate Chemistry
dataset
posted on 2009-01-12, 00:00 authored by Joanna Haywood, James V. Morey, Andrew E. H. Wheatley, Ching-Yuan Liu, Shuji Yasuike, Jyoji Kurita, Masanobu Uchiyama, Paul R. RaithbyCuCN reacts with RLi and TMPLi (TMP = 2,2,6,6-tetramethylpiperidide) to give Gilman-type cuprates R(TMP)CuLi·nL (R = Ph, n = 3, L = THF 2; R = Me, n = 1, L = TMEDA 3). 3 and 3·LiCN have been tested in directed ortho cupration with data suggesting enhanced efficiency for Lipshutz-type 3·LiCN; competition between Lipshutz- and Gilman-type formulations is rationalized by DFT methods.
