Copper-CatalyzedCross-Coupling of Bicyclobutaneswith Triftosylhydrazone Leading to Skipped Dienes

Here, we report a protocol for the synthesis of skipped dienes through the cross-coupling of bicyclo[1.1.0]­butanes with trifluoromethyl triftosylhydrazones. The reaction is run using Tp<sup>Br3</sup>Cu­(NCMe) as a catalyst to give access to a library of trifluoromethylated skipped dienes (32 examples, ≤98% yield) with excellent <i>E</i>/<i>Z</i> selectivity under mild and operationally safe conditions. The presented methods proved to be compatible with various functionalized bicyclo[1.1.0]­butanes and triftosylhydrazones.

Publication Details

Journal
Figshare
Published
2025-03-05
DOI
https://doi.org/10.1021/acs.orglett.4c04519.s001
Primary Topic
Educational Robotics and Engineering
Type
article
Field-Weighted Citation Impact
0.00
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article

Copper-CatalyzedCross-Coupling of Bicyclobutaneswith Triftosylhydrazone Leading to Skipped Dienes

Figshare
Educational Robotics and Engineering
article

Copper-CatalyzedCross-Coupling of Bicyclobutaneswith Triftosylhydrazone Leading to Skipped Dienes

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Abstract

Here, we report a protocol for the synthesis of skipped dienes through the cross-coupling of bicyclo[1.1.0]­butanes with trifluoromethyl triftosylhydrazones. The reaction is run using Tp<sup>Br3</sup>Cu­(NCMe) as a catalyst to give access to a library of trifluoromethylated skipped dienes (32 examples, ≤98% yield) with excellent <i>E</i>/<i>Z</i> selectivity under mild and operationally safe conditions. The presented methods proved to be compatible with various functionalized bicyclo[1.1.0]­butanes and triftosylhydrazones.

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Clean water and sanitation
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Educational Robotics and Engineering
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Copper-CatalyzedCross-Coupling of Bicyclobutaneswith Triftosylhydrazone Leading to Skipped Dienes · Figshare (2025) | TGRS Research Map | TGRS