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Iron-Catalyzed Alkenylzincation of Internal Alkynes
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  • Wei-Na Wang,
  • Qiang Huang,
  • Ye Jin,
  • Qi-Lin Zhou,
  • Shoufei Zhu
Wei-Na Wang
Nankai University
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Qiang Huang
Nankai University
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Ye Jin
Nankai University
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Qi-Lin Zhou
Nankai University
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Shoufei Zhu
Nankai University

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Abstract

The alkenylzincation of internal alkynes is an effective method for the synthesis of multi-substituted conjugated dienes; however, the current catalytic systems for this reaction are limited in terms of substrate scope and selectivity control, which restricts its practical applications. Herein, we report the first iron-catalyzed alkenylzincation of internal alkynes, which features mild conditions, simple oper-ation, broad substrate scope (including aryl/alkyl, diaryl, and dialkyl acetylenes), excellent functional group tolerance (tolerating highly active functional groups such as ester, methylthio, amide, sulfonyl, cyano, etc), and high activity (with a turnover number of up to 11500, the highest record for carbometallation reactions). Notably, the catalytic system described in this article also realized the highly selective vinylzincation of unfunctionalized internal alkynes as well as the alkenylzincation of unsymmetrical diarylacetylenes and dial-kyl acetylenes, which have not been achieved with other catalytic systems reported in the literatures. The current study provides a highly selective access to synthetically important multi-substituted conjugated dienes.
09 Aug 20231st Revision Received
09 Aug 2023Assigned to Editor
09 Aug 2023Submission Checks Completed
09 Aug 2023Review(s) Completed, Editorial Evaluation Pending
10 Aug 2023Editorial Decision: Accept