Gilman-type versus Lipshutz-type reagents: Competition in lithiocuprate chemistry

Joanna Haywood, James V. Morey, E. H.Andrew Wheatley, Ching Yuan Liu, Shuji Yasuike, Jyoji Kurita, Masanobu Uchiyama, Paul R. Raithby

Research output: Contribution to journalArticlepeer-review

29 Scopus citations

Abstract

CuCN 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.

Original languageEnglish
Pages (from-to)38-41
Number of pages4
JournalOrganometallics
Volume28
Issue number1
DOIs
StatePublished - 12 Jan 2009

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