Gilman-Type versus Lipshutz-Type Reagents: Competition in Lithiocuprate Chemistry

J Haywood; J V Morey; A E H Wheatley; C Y Liu; S Yasuike; J Kurita; M Uchiyama; Paul R Raithby

doi:10.1021/om801101u

Gilman-Type versus Lipshutz-Type Reagents: Competition in Lithiocuprate Chemistry

J Haywood, J V Morey, A E H Wheatley, C Y Liu, S Yasuike, J Kurita, M Uchiyama, Paul R Raithby

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

31 Citations (SciVal)

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 language	English
Pages (from-to)	38-41
Number of pages	4
Journal	Organometallics
Volume	28
Issue number	1
DOIs	https://doi.org/10.1021/om801101u
Publication status	Published - 2009

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title = "Gilman-Type versus Lipshutz-Type Reagents: Competition in Lithiocuprate Chemistry",

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.",

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T1 - Gilman-Type versus Lipshutz-Type Reagents: Competition in Lithiocuprate Chemistry

AU - Haywood, J

AU - Morey, J V

AU - Wheatley, A E H

AU - Liu, C Y

AU - Yasuike, S

AU - Kurita, J

AU - Uchiyama, M

AU - Raithby, Paul R

PY - 2009

Y1 - 2009

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/61849101467

UR - http://dx.doi.org/10.1021/om801101u

U2 - 10.1021/om801101u

DO - 10.1021/om801101u

M3 - Article

SN - 0276-7333

VL - 28

SP - 38

EP - 41

JO - Organometallics

JF - Organometallics

IS - 1

ER -

Gilman-Type versus Lipshutz-Type Reagents: Competition in Lithiocuprate Chemistry

Abstract

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