Anhydrous ZnCl2: A Highly Efficient Reagent for Facile and Regioselective Conversion of Epoxides to β-Chlorohydrins

Ronak Eisavi,Behzad Zeynizadeh,Mehri Kouhkan

doi:10.5267/j.ccl.2015.10.001

Ronak Eisavi, Behzad Zeynizadeh + Show 1 more

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https://doi.org/10.5267/j.ccl.2015.10.001

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Abstract

Article history: Received July 21, 2015 Received in revised form August 29, 2015 Accepted 19 September 2015 Available online 20 September 2015 Facile conversion of structurally different epoxides to the corresponding β-chlorohydrins was carried out successfully with anhydrous ZnCl2 in CH3CN. The reactions were carried out within 10-50 min to give β-chlorohydrins with perfect regioselectivity and high yields (8097%). © 2015Growing Science Ltd. All rights reserved.

Highlights

Introduction βChlorohydrins are one of the most versatile intermediates in organic synthesis to achieve a variety of functional groups,[1] halogenated marine products,[2] chiral auxiliaries,[3] biologically active compounds[4] including lipid mediators,[5,6,7,8,9] and unnatural amino acids.[10]
Eisavi) silicagel,[16] TCT/morpholine,[17] TMSCl/ZnO,[18] NbCl5,19 TMSCl/[bmim][PF6],20 SiCl4/chiral bipyridine N,N'-dioxides,[21] HCl/(salen)Co,[22] TMSCl/(R)-(+)-BINOL-Ti,[23] ClPPh2,24 AlCl3,25 NH4Cl/LiClO4,26 BiCl3,27 BHBr2-SMe2,28 HX or LiX/β-cyclodextrine,[29] chloride ion/halohydrin dehalogenase,[30] Cl2/phenyl hydrazine,[31] ZrCl4,32 InBr3,33 TMSCl/phosphazirconocene,[34] TMSCl/phosphaferrocene,[35] LiClO4,36 polyvinylpyrolidone/thionylchloride,[37] and La(NO3)3·6H2O38 are some of the reagents which have been used for the preparation of β-chlorohydrins from epoxides
A literature review shows that though the preparation of chlorohydrins form epoxides has been achieved by various metal halides (LiCl, NbCl5, SiCl4, AlCl3, BiCl3 and ZrCl4), the capability of anhydrous ZnCl2 for regioselective conversion of epoxides into β-chlorohydrins has not been investigated yet

Summary

Introduction

Introduction βChlorohydrins are one of the most versatile intermediates in organic synthesis to achieve a variety of functional groups,[1] halogenated marine products,[2] chiral auxiliaries,[3] biologically active compounds[4] including lipid mediators,[5,6,7,8,9] and unnatural amino acids.[10]. ABSTRACT Facile conversion of structurally different epoxides to the corresponding β-chlorohydrins was carried out successfully with anhydrous ZnCl2 in CH3CN. The reactions were carried out within 10-50 min to give β-chlorohydrins with perfect regioselectivity and high yields (8097%).

Results

Conclusion