DDQ catalyzed benzylic acetoxylation of arylalkanes: a case of exquisitely controlled oxidation under sonochemical activation

Vinod Kumar; Abhishek Sharma; Meenakshi Sharma; Upendra K. Sharma; Arun K. Sinha

doi:10.1016/j.tet.2007.07.018

DDQ catalyzed benzylic acetoxylation of arylalkanes: a case of exquisitely controlled oxidation under sonochemical activation

Vinod Kumar, Abhishek Sharma, Meenakshi Sharma, Upendra K. Sharma, Arun K. Sinha

Department of Chemistry and Chemical Biology

CSIR - Institute of Himalayan Bioresource Technology

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

58 Scopus citations

Abstract

Acetoxylated arylalkanes are selectively obtained via sonochemical activation of DDQ catalyzed benzylic oxidation of arylalkanes in the presence of anhydrous acetic acid. The method gives an exquisite control of benzylic acetoxylation under ultrasound, in contrast to the uncontrolled oxidation observed under conventional heating or microwave activation. In addition, the developed method could be a useful strategy for the synthesis of industrially important enantiopure benzyl alcohols due to the easy amenability of obtained acetoxylated products toward chiral resolution.

Original language	English
Pages (from-to)	9718-9723
Number of pages	6
Journal	Tetrahedron
Volume	63
Issue number	39
DOIs	https://doi.org/10.1016/j.tet.2007.07.018
State	Published - 24 Sep 2007

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title = "DDQ catalyzed benzylic acetoxylation of arylalkanes: a case of exquisitely controlled oxidation under sonochemical activation",

abstract = "Acetoxylated arylalkanes are selectively obtained via sonochemical activation of DDQ catalyzed benzylic oxidation of arylalkanes in the presence of anhydrous acetic acid. The method gives an exquisite control of benzylic acetoxylation under ultrasound, in contrast to the uncontrolled oxidation observed under conventional heating or microwave activation. In addition, the developed method could be a useful strategy for the synthesis of industrially important enantiopure benzyl alcohols due to the easy amenability of obtained acetoxylated products toward chiral resolution.",

author = "Vinod Kumar and Abhishek Sharma and Meenakshi Sharma and Sharma, {Upendra K.} and Sinha, {Arun K.}",

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T1 - DDQ catalyzed benzylic acetoxylation of arylalkanes

T2 - a case of exquisitely controlled oxidation under sonochemical activation

AU - Kumar, Vinod

AU - Sharma, Abhishek

AU - Sharma, Meenakshi

AU - Sharma, Upendra K.

AU - Sinha, Arun K.

PY - 2007/9/24

Y1 - 2007/9/24

N2 - Acetoxylated arylalkanes are selectively obtained via sonochemical activation of DDQ catalyzed benzylic oxidation of arylalkanes in the presence of anhydrous acetic acid. The method gives an exquisite control of benzylic acetoxylation under ultrasound, in contrast to the uncontrolled oxidation observed under conventional heating or microwave activation. In addition, the developed method could be a useful strategy for the synthesis of industrially important enantiopure benzyl alcohols due to the easy amenability of obtained acetoxylated products toward chiral resolution.

AB - Acetoxylated arylalkanes are selectively obtained via sonochemical activation of DDQ catalyzed benzylic oxidation of arylalkanes in the presence of anhydrous acetic acid. The method gives an exquisite control of benzylic acetoxylation under ultrasound, in contrast to the uncontrolled oxidation observed under conventional heating or microwave activation. In addition, the developed method could be a useful strategy for the synthesis of industrially important enantiopure benzyl alcohols due to the easy amenability of obtained acetoxylated products toward chiral resolution.

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DO - 10.1016/j.tet.2007.07.018

M3 - Article

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SN - 0040-4020

VL - 63

SP - 9718

EP - 9723

JO - Tetrahedron

JF - Tetrahedron

IS - 39

ER -

DDQ catalyzed benzylic acetoxylation of arylalkanes: a case of exquisitely controlled oxidation under sonochemical activation

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