Viewed: 17:51:32 in March 29, 2020

Virtues of Volatility: A Facile Transesterification Approach to Boronic Acids (Hinkes, Stefan; Klein, Christian D. P.)
Org. Lett. 2019, 21 (9), 3048−3052.

Keywords: methylboronic acid; deprotection; dichloromethane; trifluoroacetic acid

ボロン酸エステルの脱保護について報告しています。脱保護、つまり、エステル分解の方法が少し変わっていて、メチルボロン酸(ボロン酸エステルではない)を使います。広義のエステル交換反応のようなそうでないような。反応後にメチルボロン酸やその成れの果てを40℃で減圧留去すれば脱保護されたボロン酸が得られるというのが売りのようです。

ボロン酸だけで簡単に脱保護ができるものかねえとSupporting Informationを眺めました。トリフルオロ酢酸のジクロロメタン溶液中(場合によっては希塩酸/アセトン)で反応を行なっていますね。メチルボロン酸が基質に対して過剰量使われています。

ボロン酸ですが、脱水反応で酸無水物が生成することがしばしばあるので、そのあたりのところをどう回避しているのかなあと思いましたが、「仕上げ」に希塩酸水溶液を加えて水などを減圧留去し、残ったものを乾燥している模様。

Supporting Informationを眺めていて思ったのは、「含窒素化合物の例が多いな」というもの。なんでまたそんなものをと思ったので、読みたい論文に追加です。

ジボロンがかわいそうなことに。

 

Bogerピリジン合成 [Doi 1]
Corey−Itsuno還元 [Doi 1]
Danheiser環化 [Doi 1]
Hiraoカップリング [Doi 1]
Schöllkopf法 [Doi 1]
化学反応過程の理論的研究
(Kenichi Fukui, Roald Hoffmann)
スペースシャトル・コロンビアが初のスペースシャトルミッションで打ち上げ
パラオが自治領となる
最初のAIDS患者発見例
マハティール・ビン・モハマドがマレーシア首相となる
ダイアナ妃、チャールズ・ウィンザー(イギリス王子)と結婚
IBMがマイクロソフトのDOS搭載の「IBM PC」を発表
中国残留孤児が初来日
「力うどん」発売(エースコック)
日本初の新交通システムが神戸市で営業開始
ピンク・レディーが解散
「Dr.スランプ アラレちゃん」放送開始(フジテレビ)
「名犬ジョリィ放映開始」(NHK)
「オレたちひょうきん族」放送開始(フジテレビ)
「ドライペット」発売(エステー化学=エステー)
「常用漢字表」告示
「まんが水戸黄門」放映開始(東京12チャンネル=テレビ東京)
東京12チャンネルがテレビ東京に社名変更
「リアルゴールド」発売(日本コカ・コーラ)
「雪見だいふく」発売(ロッテ)
「なるほど!ザ・ワールド」放送開始(フジテレビ)
「じゃりン子チエ」放映開始(毎日放送)
「うる星やつら」放映開始(フジテレビ)
「FOCUS」創刊(新潮社)
ロス疑惑
「セーラー服と機関銃」上映
「北の国から」放送(フジテレビ)

 

ここの画像を使用しています。

ちょっとかっこよくなった短足キジトラ。。

 

Just finished the calculations: 6,7-dihydroxycoumarin (esculetin) https://t.co/Mu5U7IGsVE pic.twitter.com/dvsQtAO2Zw

— nanoniele (@nanoniele) May 17, 2019

 

　

 

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