スタニル・リチウム: 容易で効率的な合成により,さらなる応用が容易になる
Dong-Yu Wang1,2, Chao Wang1,2, Masanobu Uchiyama1,2
1Graduate School of Pharmaceutical Sciences, University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo-to 113-0033, Japan.
Journal of the American Chemical Society
|July 29, 2015
まとめ
新しいポリサイクル芳香炭化水素触媒法により,室温でチンの前体からスタニルリチウム (Sn-Li) を効率的に合成する. この安定した高反応性Sn-Li反応剤は 化学合成の環境にやさしい代替手段となります
科学分野:
- 有機金属化学
- 合成化学
背景:
- 伝統的なオルガノチン化合物の合成には 有毒な副産物と厳しい条件が伴います
- 主要な有機金属反応剤の効率的で環境に害のない合成経路の開発は極めて重要です.
研究 の 目的:
- スタニルリチウム (Sn-Li) の実用的で高効率の触媒合成を開発する.
- 高い原子経済性と安定性を持つSn-Li生成のための室温方法を確立する.
主な方法:
- ポリサイクルアロマティック炭化水素 (PAH) を,チンの前駆体変換の触媒として使用した.
- スタニル塩化物やディスタニルを使用しています.
- 室温で反応し,有毒な副産物を生成しない.
主要な成果:
- スタンニルリチウム (Sn-Li) 試料への素早く定量的変換を達成した.
- 合成されたSn-Li反応剤は,様々な基板に対して高い反応性を示した.
- スタニルリチウム反応剤は安定性があり,環境温度で長期間 (数ヶ月) 保存することが可能であった.
- 合成プロセスは,定量的原子効率を達成しました.
結論:
- 開発されたPAH触媒合成は,スタニルリチウムへの非常に効率的で実用的でグリーンな経路を提供します.
- この方法は有毒な副産物を避け,様々な合成用途のための安定した反応性オルガノチン反応剤を提供します.
関連する概念動画
02:27Preparation of Alkynes: Alkylation Reaction
12.7K
Introduction
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.
12.7K
02:26Preparation and Reactions of Sulfides
6.0K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
6.0K
01:20Anionic Chain-Growth Polymerization: Overview
2.8K
The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
2.8K
01:04Anionic Chain-Growth Polymerization: Mechanism
2.6K
The mechanism for anionic chain-growth polymerization involves initiation, propagation, and termination steps. In the initiation step, a nucleophilic anion, such as butyl lithium, initiates the polymerization process by attacking the π bond of the vinylic monomer. As a result, a carbanion, stabilized by the electron‐withdrawing group, is generated. The resulting carbanion acts as a Michael donor in the propagation step and attacks the second vinylic monomer, which acts as a Michael...
2.6K
01:15Acid Halides to Alcohols: Grignard Reaction
3.4K
Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the Grignard reagent and proceeds via a ketone intermediate.
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...
3.4K
00:56Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction
2.9K
The reaction between two different carbonyl compounds comprising α hydrogen in the presence of a strong base like lithium diisopropylamide (LDA) to form a crossed aldol product is known as a directed aldol reaction. The directed aldol reaction is depicted in Figure 1.
2.9K