Leaving group dependence of the rates of halogen-magnesium exchange reactions

Lei Shi; Yuanyuan Chu; Paul Knochel; Herbert Mayr

doi:10.1021/ol300906a

Leaving group dependence of the rates of halogen-magnesium exchange reactions

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

^*Corresponding author for this work

School of Sciences

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

28 Scopus citations

Abstract

Relative reactivities and absolute rate constants of the reactions of haloarenes with i-PrMgCl•LiCl were investigated in THF at 0 °C. The rate of the halogen-magnesium exchange decreases in the series ArI > ArBr > ArCl (relative reactivities: 10 ¹¹:10 ⁶:1). Preliminary experiments show that the p-tolylsulfinyl group is exchanged slightly faster than iodide, while a tosyl group is exchanged at least 10 ⁴ times more slowly than a bromide.

Original language	English
Pages (from-to)	2602-2605
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	10
DOIs	https://doi.org/10.1021/ol300906a
State	Published - 18 May 2012

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title = "Leaving group dependence of the rates of halogen-magnesium exchange reactions",

abstract = "Relative reactivities and absolute rate constants of the reactions of haloarenes with i-PrMgCl•LiCl were investigated in THF at 0 °C. The rate of the halogen-magnesium exchange decreases in the series ArI > ArBr > ArCl (relative reactivities: 10 11:10 6:1). Preliminary experiments show that the p-tolylsulfinyl group is exchanged slightly faster than iodide, while a tosyl group is exchanged at least 10 4 times more slowly than a bromide.",

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

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doi = "10.1021/ol300906a",

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AU - Shi, Lei

AU - Chu, Yuanyuan

AU - Knochel, Paul

AU - Mayr, Herbert

PY - 2012/5/18

Y1 - 2012/5/18

N2 - Relative reactivities and absolute rate constants of the reactions of haloarenes with i-PrMgCl•LiCl were investigated in THF at 0 °C. The rate of the halogen-magnesium exchange decreases in the series ArI > ArBr > ArCl (relative reactivities: 10 11:10 6:1). Preliminary experiments show that the p-tolylsulfinyl group is exchanged slightly faster than iodide, while a tosyl group is exchanged at least 10 4 times more slowly than a bromide.

AB - Relative reactivities and absolute rate constants of the reactions of haloarenes with i-PrMgCl•LiCl were investigated in THF at 0 °C. The rate of the halogen-magnesium exchange decreases in the series ArI > ArBr > ArCl (relative reactivities: 10 11:10 6:1). Preliminary experiments show that the p-tolylsulfinyl group is exchanged slightly faster than iodide, while a tosyl group is exchanged at least 10 4 times more slowly than a bromide.

UR - https://www.scopus.com/pages/publications/84862099497

U2 - 10.1021/ol300906a

DO - 10.1021/ol300906a

M3 - 文章

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VL - 14

SP - 2602

EP - 2605

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

Leaving group dependence of the rates of halogen-magnesium exchange reactions

Abstract

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