C-C多重結合の金属無転移水酸化
Weiqiang Chen1, Johannes C L Walker1, Martin Oestreich1
1Institut für Chemie , Technische Universität Berlin , Strasse des 17. Juni 115 , 10623 Berlin , Germany.
Journal of the American Chemical Society
|December 15, 2018
まとめ
新しいサイクロヘキサ-1,4-ダイネ基化合物は,水酸化反応のためにヨウ素を安全に供給します. この方法は危険なヨウ素酸化ガスを避け,様々なビニルヨウ素を合成することができる.
科学分野:
- 有機化学
- 合成化学
背景:
- ガス状のヨウ素 (HI) は,水酸化に役立つ反応剤であるが,扱いは危険である.
- 現存する HI in situ 生成方法は,しばしば複雑な手順や不安定な前体を含みます.
研究 の 目的:
- 安定したベンチトップの代替物を設計し合成する.
- この代替品を使って 安全で効率的な水酸化プロトコルを開発する
主な方法:
- サイクロヘキサ-1, 4- ディエンの派生物は,グラムスケールで合成された.
- 代理物質は,様々なアルキンとアレンと,ブロンステッド酸触媒で反応した.
- 反応産物と副産物を分析した.
主要な成果:
- サイクロヘキサ-1,4-ダイネ基の代用剤は,ヨウ素をC−C多重結合に効果的に転送した.
- 反応は,自由のヨウ素やヨウ素酸を必要とせずに進行した.
- 代替物は揮発性トルーエンとエチレンに分解され,浄化が簡素化されます.
- 以前は入手不可能だったビニルヨーデートは,ステレオ制御で合成された.
結論:
- ガス状のヨウ素水素化に対する安全で実用的な代替手段が開発された.
- この方法は,様々なビニルヨーデートのステレオ制御合成を容易にする.
- 開発されたプロトコルは,有機合成のための危険な反応剤の処理に重要な進歩をもたらします.
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