Efficient and selective Stille cross-coupling of benzylic and allylic bromides using bromobis(triphenylphosphine) (N-succinimide)palladium(II)

C M  Crawforth; I J S  Fairlamb; R J K  Taylor

doi:10.1016/j.tetlet.2003.11.014

Efficient and selective Stille cross-coupling of benzylic and allylic bromides using bromobis(triphenylphosphine) (N-succinimide)palladium(II)

C M Crawforth, I J S Fairlamb, R J K Taylor

Chemistry

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

Abstract

Allylic and benzylic bromides are cross-coupled with organostannanes efficiently using the precatalyst [Pd(NCOC2H4CO)(PPh3)(2)Br] 1. Significantly, these reactions do not require the use of hexamethylphosphoramide (HMPA) as the solvent, or additional ligands, such as trifurylphosphine or triphenylarsine. Selectivity for benzyl bromide over bromobenzene is observed for precatalyst 1, against the precatalysts, bromobis(triphenylphosphine)(benzyl)palladium(II) and bis(triphenylphosphine)palladium(II) bromide. (C) 2003 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	461-465
Number of pages	5
Journal	Tetrahedron Letters
Volume	45
Issue number	3
DOIs	https://doi.org/10.1016/j.tetlet.2003.11.014
Publication status	Published - 12 Jan 2004

Keywords

ORGANOTIN COMPOUNDS
PALLADIUM
CHLORIDES
LIGANDS
BOND
REACTIVITY
ALKYLATION
CATALYSIS
COMPLEXES
REAGENTS

Access to Document

10.1016/j.tetlet.2003.11.014

Cite this

@article{e9c08588e806447a968f8bf487e20277,

title = "Efficient and selective Stille cross-coupling of benzylic and allylic bromides using bromobis(triphenylphosphine) (N-succinimide)palladium(II)",

abstract = "Allylic and benzylic bromides are cross-coupled with organostannanes efficiently using the precatalyst [Pd(NCOC2H4CO)(PPh3)(2)Br] 1. Significantly, these reactions do not require the use of hexamethylphosphoramide (HMPA) as the solvent, or additional ligands, such as trifurylphosphine or triphenylarsine. Selectivity for benzyl bromide over bromobenzene is observed for precatalyst 1, against the precatalysts, bromobis(triphenylphosphine)(benzyl)palladium(II) and bis(triphenylphosphine)palladium(II) bromide. (C) 2003 Elsevier Ltd. All rights reserved.",

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author = "Crawforth, {C M} and Fairlamb, {I J S} and Taylor, {R J K}",

year = "2004",

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day = "12",

doi = "10.1016/j.tetlet.2003.11.014",

language = "English",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Efficient and selective Stille cross-coupling of benzylic and allylic bromides using bromobis(triphenylphosphine) (N-succinimide)palladium(II)

AU - Crawforth, C M

AU - Fairlamb, I J S

AU - Taylor, R J K

PY - 2004/1/12

Y1 - 2004/1/12

N2 - Allylic and benzylic bromides are cross-coupled with organostannanes efficiently using the precatalyst [Pd(NCOC2H4CO)(PPh3)(2)Br] 1. Significantly, these reactions do not require the use of hexamethylphosphoramide (HMPA) as the solvent, or additional ligands, such as trifurylphosphine or triphenylarsine. Selectivity for benzyl bromide over bromobenzene is observed for precatalyst 1, against the precatalysts, bromobis(triphenylphosphine)(benzyl)palladium(II) and bis(triphenylphosphine)palladium(II) bromide. (C) 2003 Elsevier Ltd. All rights reserved.

AB - Allylic and benzylic bromides are cross-coupled with organostannanes efficiently using the precatalyst [Pd(NCOC2H4CO)(PPh3)(2)Br] 1. Significantly, these reactions do not require the use of hexamethylphosphoramide (HMPA) as the solvent, or additional ligands, such as trifurylphosphine or triphenylarsine. Selectivity for benzyl bromide over bromobenzene is observed for precatalyst 1, against the precatalysts, bromobis(triphenylphosphine)(benzyl)palladium(II) and bis(triphenylphosphine)palladium(II) bromide. (C) 2003 Elsevier Ltd. All rights reserved.

KW - ORGANOTIN COMPOUNDS

KW - PALLADIUM

KW - CHLORIDES

KW - LIGANDS

KW - BOND

KW - REACTIVITY

KW - ALKYLATION

KW - CATALYSIS

KW - COMPLEXES

KW - REAGENTS

U2 - 10.1016/j.tetlet.2003.11.014

DO - 10.1016/j.tetlet.2003.11.014

M3 - Article

SN - 0040-4039

VL - 45

SP - 461

EP - 465

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 3

ER -