黄金催化了arenyne-yne功能的分子内 [3 + 2] - 循环添加
Jian-Jou Lian1, Po-Chiang Chen, Yau-Ping Lin
1Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, Republic of China.
Journal of the American Chemical Society
|August 31, 2006
概括
一种新的黄金催化反应有效地从简单的前体中产生复杂的分子. 这种分子内循环添加在温和条件下对各种代因基质有效.
科学领域:
- 有机化学 有机化学
- 催化剂是一种催化剂.
- 合成方法论 合成方法论
背景情况:
- 内分子循环添加是构建循环有机分子的强大工具.
- 开发高效的催化系统未被激活的基质仍然是一个挑战在有机合成.
研究的目的:
- 报告一个新的,高效的分子内 [3+2] - 循环添加反应.
- 为了证明黄金催化在这种转化中的实用性.
主要方法:
- 使用AuPPh3SbF6复合物作为催化剂 (2mol %).
- 在环境条件下进行反应.
- 采用一系列具有不同功能组的二烯基基底.
主要成果:
- 实现了未激活的arenyne (或enyne) -yne功能性的有效的分子内 [3+2]-循环添加.
- 已证明具有广泛的基质范围,可以容忍 diyne 起始材料上的各种功能组.
- 在温和的环境条件下,反应有效地进行.
结论:
- 报告的黄金催化循环添加提供了一种有价值的新方法来合成复杂的有机结构.
- 反应的效率和功能组耐受性使其成为合成化学家的一种多功能工具.
相关概念视频
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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
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Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
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Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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