Relative rates of bromine-magnesium exchange reactions in substituted bromobenzene derivatives

Lei Shi; Yuanyuan Chu; Paul Knochel; Herbert Mayr

doi:10.1002/anie.200704100

Relative rates of bromine-magnesium exchange reactions in substituted bromobenzene derivatives

Lei Shi^*
, Yuanyuan Chu
, Paul Knochel
, Herbert Mayr

^*Corresponding author for this work

Ludwig Maximilian University of Munich

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

55 Scopus citations

Abstract

(Chemical Equation Presented) Against expectation: How can the site of Br-Mg exchange in multiply brominated compounds be predicted? Competition experiments with different substituents X and Y (see scheme; X, Y = H, F, Cl, Br, CF₃, CO₂tBu, CN) reveal a counterintuitive order of substituent effects. The aim of the study is to enable the selectivity of halogen-magnesium exchange reactions of polyfunctional compounds to be predicted.

Original language	English
Pages (from-to)	202-204
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	1
DOIs	https://doi.org/10.1002/anie.200704100
State	Published - 2008
Externally published	Yes

Keywords

Bromine-magnesium exchange
Competition experiments
Grignard reactions
Lithium
Regioselectivity

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10.1002/anie.200704100

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title = "Relative rates of bromine-magnesium exchange reactions in substituted bromobenzene derivatives",

abstract = "(Chemical Equation Presented) Against expectation: How can the site of Br-Mg exchange in multiply brominated compounds be predicted? Competition experiments with different substituents X and Y (see scheme; X, Y = H, F, Cl, Br, CF3, CO2tBu, CN) reveal a counterintuitive order of substituent effects. The aim of the study is to enable the selectivity of halogen-magnesium exchange reactions of polyfunctional compounds to be predicted.",

keywords = "Bromine-magnesium exchange, Competition experiments, Grignard reactions, Lithium, Regioselectivity",

author = "Lei Shi and Yuanyuan Chu and Paul Knochel and Herbert Mayr",

year = "2008",

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AU - Shi, Lei

AU - Chu, Yuanyuan

AU - Knochel, Paul

AU - Mayr, Herbert

PY - 2008

Y1 - 2008

N2 - (Chemical Equation Presented) Against expectation: How can the site of Br-Mg exchange in multiply brominated compounds be predicted? Competition experiments with different substituents X and Y (see scheme; X, Y = H, F, Cl, Br, CF3, CO2tBu, CN) reveal a counterintuitive order of substituent effects. The aim of the study is to enable the selectivity of halogen-magnesium exchange reactions of polyfunctional compounds to be predicted.

AB - (Chemical Equation Presented) Against expectation: How can the site of Br-Mg exchange in multiply brominated compounds be predicted? Competition experiments with different substituents X and Y (see scheme; X, Y = H, F, Cl, Br, CF3, CO2tBu, CN) reveal a counterintuitive order of substituent effects. The aim of the study is to enable the selectivity of halogen-magnesium exchange reactions of polyfunctional compounds to be predicted.

KW - Bromine-magnesium exchange

KW - Competition experiments

KW - Grignard reactions

KW - Lithium

KW - Regioselectivity

UR - https://www.scopus.com/pages/publications/37549000558

U2 - 10.1002/anie.200704100

DO - 10.1002/anie.200704100

M3 - 文章

AN - SCOPUS:37549000558

SN - 1433-7851

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SP - 202

EP - 204

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 1

ER -

Relative rates of bromine-magnesium exchange reactions in substituted bromobenzene derivatives

Abstract

Keywords

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