通过催化剂对多环芳的直接化
Kenji Mochida1, Katsuaki Kawasumi, Yasutomo Segawa
1Department of Chemistry, Graduate School of Science, Nagoya University, Nagoya 464-8602, Japan.
Journal of the American Chemical Society
|June 25, 2011
概括
我们发现了一种新的方法,可以直接将基连接到多环芳 (PAH) 的K区域. 这一过程有效地扩展了PAHs的π-系统,并具有精确的控制.
科学领域:
- 有机化学 有机化学
- 催化剂是一种催化剂.
- 材料科学 材料科学 材料科学
背景情况:
- 多环芳 (PAH) 在材料科学和有机电子学中至关重要.
- 直接的C-H键功能化提供了一种有效的途径来修改复杂的有机分子.
- 选择性功能化PAHs,特别是在K区域,仍然是一个合成的挑战.
研究的目的:
- 开发一种催化系统,用于PAHs的直接C-H化.
- 为了在PAHs的K区域实现选择性化.
- 为了探索对π系统扩展的arylation和cyclodehydrogenation的顺序组合.
主要方法:
- 使用了乙酸 (PdOAc) 和o-chloranil催化系统.
- 使用阿里尔博洛克辛作为阿里化试剂.
- 集成的Palladium催化直接化与FeCl(3) 介导的循环脱化.
主要成果:
- 在K区域选择性地实现了PAHs的直接C-H键合.
- 证明了顺序Pd催化和FeCl(3) 中介循环脱的有效性.
- 成功地扩展了具有高定向性的父PAHs的π系统.
结论:
- 这种Pd(OAc) ((2) /o-chloranil系统能够选择性地对PAHs进行K-区域的配合.
- 连续的化和循环脱化为π系统扩张提供了一个强大的策略.
- 这种方法为合成扩展的多环芳香系统提供了精确的控制.
相关概念视频
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Introduction
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.
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.
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
Reduction of Alkenes: Catalytic Hydrogenation
Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the surface of...
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the surface of...
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)
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.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Preparation of Alkynes: Dehydrohalogenation
Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.


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