Room Temperature Allenation of Terminal Alkynes with Aldehydes
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- Junzhe Xiao
- State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 P. R. China
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- Yifan Cui
- State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 P. R. China
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- Can Li
- State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 P. R. China
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- Haibo Xu
- State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 P. R. China
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- Yizhan Zhai
- State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 P. R. China
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- Xue Zhang
- State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 P. R. China
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- Shengming Ma
- State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 P. R. China
Abstract
<jats:title>Abstract</jats:title><jats:p>A gold‐catalyzed room temperature allenation of terminal alkynes (ATA) with aldehydes affording 1,3‐disubstituted allenes with diverse functional groups has been developed by identifying a gold(I) catalyst and an amine. The practicality of this reaction has been demonstrated by a ten gram‐scale synthesis and the synthetic potentials have been demonstrated via various transformations and formal total synthesis of (−)‐centrolobine. Mechanistic studies revealed that the gold catalyst, the aldehyde effect, the fluoroalkyl hydroxyl solvent (TFE or HFIP) and the structure of amine are vital in this room temperature ATA reaction.</jats:p>
Journal
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- Angewandte Chemie International Edition
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Angewandte Chemie International Edition 60 (49), 25708-25713, 2021-11-03
Wiley
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Details 詳細情報について
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- CRID
- 1360580239596812032
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- ISSN
- 15213773
- 14337851
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- Data Source
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- Crossref