A Facile Preparation of Tetrasubstituted Arylalkenes Catalyzed by <i>p</i> ‐Toluenesulfonic Acid Monohydrate ( <i>p</i> ‐TsOH⋅H <sub>2</sub> O): Application in the Synthesis of the Intermediate of Tamoxifen

Abstract An efficient synthesis of tetrasubstituted arylalkenes was readily achieved by the reaction of α‐( tert ‐butyl)benzylic alcohols using p ‐toluenensulfonic acid monohydrate as a Brønsted acid. A broad range of substrates was applicable for the reaction in good yield with high regioselectivity. The key intermediate in the synthesis of tamoxifen was produced using the present method as an example, and a plausible reaction mechanism was proposed by examining the reaction intermediates.

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Publication Details

Journal
ChemistrySelect
Published
2024-09-13
DOI
https://doi.org/10.1002/slct.202402951
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
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article

A Facile Preparation of Tetrasubstituted Arylalkenes Catalyzed by p ‐Toluenesulfonic Acid Monohydrate ( p ‐TsOH⋅H 2 O): Application in the Synthesis of the Intermediate of Tamoxifen

Kenya Nakata, Tomohiro Sutani, N. Kimura
ChemistrySelect
Catalytic Cross-Coupling Reactions
article

A Facile Preparation of Tetrasubstituted Arylalkenes Catalyzed by p ‐Toluenesulfonic Acid Monohydrate ( p ‐TsOH⋅H 2 O): Application in the Synthesis of the Intermediate of Tamoxifen

Kenya Nakata, Tomohiro Sutani, N. Kimura
article en

Abstract

Abstract An efficient synthesis of tetrasubstituted arylalkenes was readily achieved by the reaction of α‐( tert ‐butyl)benzylic alcohols using p ‐toluenensulfonic acid monohydrate as a Brønsted acid. A broad range of substrates was applicable for the reaction in good yield with high regioselectivity. The key intermediate in the synthesis of tamoxifen was produced using the present method as an example, and a plausible reaction mechanism was proposed by examining the reaction intermediates.

ChemistrySelectVol. 9(35)
Shimane University (JP)
Openalex Percentile: Top 89%
Catalytic Cross-Coupling Reactions
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