A novel copper (i) mediated, symmetrical coupling procedure for alkyl, aryl, benzyl, and thiophenyl dihalides

David K. Johnson; Jeffrey P. Ciavarri; Faoud T. Ishmael; Kurl J. Schillinger; Thomas A.P. van Geel; Stephen M. Stratton

doi:10.1016/0040-4039(95)01850-H

A novel copper (i) mediated, symmetrical coupling procedure for alkyl, aryl, benzyl, and thiophenyl dihalides

David K. Johnson
, Jeffrey P. Ciavarri
, Faoud T. Ishmael
, Kurl J. Schillinger
, Thomas A.P. van Geel
, Stephen M. Stratton

Department of Medicine

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

19 Scopus citations

Abstract

A comparative study of Li₂CuCl₄ vs Li₂CuCl₃ mediated mono-coupling reactions of dihalide substrates with allylmangnesium bromide is reported. Higher yields were obtained with Li₂CuCl₃ and the following trends in halide reactivity were observed Br > Cl for alkyl, aryl, and thiophenyl dihalides. and benzyl halide > phenyl halide. Utilizing these trends, a symmetrical coupling procedure for alkyl. aryl benzyl and thiophenyl dihalides, simply carried out by combining the dihalide with metallic magnesium and Li₂CuCl₄ is reported.

Original language	English (US)
Pages (from-to)	8565-8568
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	47
DOIs	https://doi.org/10.1016/0040-4039(95)01850-H
State	Published - Nov 20 1995

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4039(95)01850-H

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@article{7c6e35ecd5b143e69d508ecdf6ccbd9a,

title = "A novel copper (i) mediated, symmetrical coupling procedure for alkyl, aryl, benzyl, and thiophenyl dihalides",

abstract = "A comparative study of Li2CuCl4 vs Li2CuCl3 mediated mono-coupling reactions of dihalide substrates with allylmangnesium bromide is reported. Higher yields were obtained with Li2CuCl3 and the following trends in halide reactivity were observed Br > Cl for alkyl, aryl, and thiophenyl dihalides. and benzyl halide > phenyl halide. Utilizing these trends, a symmetrical coupling procedure for alkyl. aryl benzyl and thiophenyl dihalides, simply carried out by combining the dihalide with metallic magnesium and Li2CuCl4 is reported.",

author = "Johnson, \{David K.\} and Ciavarri, \{Jeffrey P.\} and Ishmael, \{Faoud T.\} and Schillinger, \{Kurl J.\} and \{van Geel\}, \{Thomas A.P.\} and Stratton, \{Stephen M.\}",

year = "1995",

month = nov,

day = "20",

doi = "10.1016/0040-4039(95)01850-H",

language = "English (US)",

volume = "36",

pages = "8565--8568",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "47",

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TY - JOUR

T1 - A novel copper (i) mediated, symmetrical coupling procedure for alkyl, aryl, benzyl, and thiophenyl dihalides

AU - Johnson, David K.

AU - Ciavarri, Jeffrey P.

AU - Ishmael, Faoud T.

AU - Schillinger, Kurl J.

AU - van Geel, Thomas A.P.

AU - Stratton, Stephen M.

PY - 1995/11/20

Y1 - 1995/11/20

N2 - A comparative study of Li2CuCl4 vs Li2CuCl3 mediated mono-coupling reactions of dihalide substrates with allylmangnesium bromide is reported. Higher yields were obtained with Li2CuCl3 and the following trends in halide reactivity were observed Br > Cl for alkyl, aryl, and thiophenyl dihalides. and benzyl halide > phenyl halide. Utilizing these trends, a symmetrical coupling procedure for alkyl. aryl benzyl and thiophenyl dihalides, simply carried out by combining the dihalide with metallic magnesium and Li2CuCl4 is reported.

AB - A comparative study of Li2CuCl4 vs Li2CuCl3 mediated mono-coupling reactions of dihalide substrates with allylmangnesium bromide is reported. Higher yields were obtained with Li2CuCl3 and the following trends in halide reactivity were observed Br > Cl for alkyl, aryl, and thiophenyl dihalides. and benzyl halide > phenyl halide. Utilizing these trends, a symmetrical coupling procedure for alkyl. aryl benzyl and thiophenyl dihalides, simply carried out by combining the dihalide with metallic magnesium and Li2CuCl4 is reported.

UR - https://www.scopus.com/pages/publications/0028827140

UR - https://www.scopus.com/pages/publications/0028827140#tab=citedBy

U2 - 10.1016/0040-4039(95)01850-H

DO - 10.1016/0040-4039(95)01850-H

M3 - Article

AN - SCOPUS:0028827140

SN - 0040-4039

VL - 36

SP - 8565

EP - 8568

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 47

ER -

A novel copper (i) mediated, symmetrical coupling procedure for alkyl, aryl, benzyl, and thiophenyl dihalides

Abstract

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