パラジウム ((II) / cis-ArSOX触媒による非対称性アリルC-Hアルキル化
Wei Liu1, Siraj Z Ali1, Stephen E Ammann1
1Roger Adams Laboratory, Department of Chemistry , University of Illinois , Urbana , Illinois 61801 , United States.
Journal of the American Chemical Society
|August 10, 2018
まとめ
研究者は,非対称なC−Hアルキル化のための新しいパラジウム触媒 (Pd−II) /シス・アリル・スルフォキシド・オクサゾリン) を開発した. これらの触媒は,様々なヌクレオフィルとの反応において,幅広い範囲と高いエナチオ選択性を示している.
科学分野:
- 有機化学
- カタリシス
- 非対称合成
背景:
- C-Hアルキレーションは有機合成における重要な変換である.
- 非対称なC−H機能化のための効率的で選択的な触媒の開発は,依然として重要な課題です.
研究 の 目的:
- シス-アリル硫酸化オクサゾリン (cis-ArSOX) リガンドを含む新しいパラジアム (II) 触媒の開発を報告する.
- 末端オレフィンの非対称C−Hアルキル化におけるこれらの触媒の応用を調査する.
主な方法:
- モジュラーで調節可能な cis-ArSOX リガンドの合成.
- Pd (II) /cis-ArSOXシステムを用いた触媒非対称C-Hアルキル化反応.
- 反応範囲,エナチオ選択性,およびダイアステレオ選択性の評価.
主要な成果:
- 37例で前例のない広範な範囲と高いエナチオ選択性 (平均> 90% ee) を達成した.
- アリファティックオレフィンのアルキル化において,高い反応性および触媒制御されたダイアステレオ選択性が実証されている.
- ArSOX基板の酸化安定性は,触媒の性能にとって極めて重要でした.
結論:
- 開発されたPd (II) /cis-ArSOX触媒は,非対称C-Hアルキル化における重要な進歩を表しています.
- この新種のキラルリガンドは,他の酸化移行金属触媒化プロセスに希望を示しています.
関連する概念動画
Catalysis
30.6K
The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
30.6K
Cis-regulatory Sequences
11.9K
Cis-regulatory sequences are short fragments of non-coding DNA that are present on the same chromosomes as the genes that they regulate. These fragments serve as binding sites for transcriptional regulators, proteins that are responsible for controlling gene transcription and differential gene expression across cell types in eukaryotes. Cis-regulatory sequences can be close to the gene of interest or thousands of bases away in the DNA sequence; however, those sequences that are further away are...
11.9K
Cis-regulatory Sequences
4.2K
4.2K
Rotation of Asymmetric Top
1.6K
By definition, a spherically symmetric body has the same moment of inertia about any axis passing through its center of mass. This situation changes if there is no spherical symmetry. Since most rigid bodies are not spherically symmetric, these require special treatment.
The relationship between the angular momentum of any rigid body and its angular velocity, both of which are vectors, involves the moment of inertia. The moment of inertia is a scalar quantity only for spherically symmetric...
The relationship between the angular momentum of any rigid body and its angular velocity, both of which are vectors, involves the moment of inertia. The moment of inertia is a scalar quantity only for spherically symmetric...
1.6K
Asymmetric Lipid Bilayer
9.9K
Biological membranes show uneven distribution of different types of lipids in the inner and outer layers, resulting in transverse asymmetric membranes. The treatment of the erythrocyte membrane with the enzyme phospholipase confirmed the asymmetric nature of the lipid bilayer. The enzyme hydrolyzes lipids into fatty acids and hydrophilic groups. The phospholipase acts only on the outer layer of the membrane, while the inner layer remains intact. The phospholipase treatment resulted in 80%...
9.9K
Alkyl Halides
20.1K
Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
20.1K


