Oxone-Mediated Regioselective Oxy-iodination of 1-Aryl/Alkyl Butadienes Using TBAI

A simple, mild, and environmentally benign regioselective oxy-iodination of 1-aryl/alkyl butadienes has been developed. While styrenes have been explored previously, this work on dienes has been highly regioselective and metal-free in oxy-iodination following Markovnikov's rule. The oxy-iodination products were obtained in good to excellent yields using various co-solvents (H<sub>2</sub>O, MeOH, EtOH, AcOH, etc.). In addition, the halohydrins have been useful building blocks in the synthesis of various functionalized keto iodides and azido alcohols.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-08-23
DOI
https://doi.org/10.1021/acs.joc.4c01439
Primary Topic
Vanadium and Halogenation Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Oxone-Mediated Regioselective Oxy-iodination of 1-Aryl/Alkyl Butadienes Using TBAI

Dnyaneshwar A. Gorve, Rodney A. Fernandes
The Journal of Organic Chemistry
Vanadium and Halogenation Chemistry
article

Oxone-Mediated Regioselective Oxy-iodination of 1-Aryl/Alkyl Butadienes Using TBAI

Dnyaneshwar A. Gorve, Rodney A. Fernandes
article en

Abstract

A simple, mild, and environmentally benign regioselective oxy-iodination of 1-aryl/alkyl butadienes has been developed. While styrenes have been explored previously, this work on dienes has been highly regioselective and metal-free in oxy-iodination following Markovnikov's rule. The oxy-iodination products were obtained in good to excellent yields using various co-solvents (H<sub>2</sub>O, MeOH, EtOH, AcOH, etc.). In addition, the halohydrins have been useful building blocks in the synthesis of various functionalized keto iodides and azido alcohols.

The Journal of Organic ChemistryVol. 89(17)
Indian Institute of Technology Bombay (IN)
Council of Scientific and Industrial Research, India, University Grants Commission
Clean water and sanitation
Openalex Percentile: Top 90%
Vanadium and Halogenation Chemistry
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