[読みたい論文] カルボン酸からの酸フルオリド合成

Viewed: 14:59:43 in December 16, 2019

Posted: March 26, 2019

[Org. Lett. 2019, 21 (6), 1659−1963] Direct Access to Acyl Fluorides from Carboxylic Acids Using a Phosphine/Fluoride Deoxyfluorination Reagent System (Munoz, Socrates; Dang, Huong; Ispizua-Rodriguez, Xanath; Mathew, Thomas; Prakash, G. K. Surya)Web: https://doi.org/10.1021/acs.orglett.9b00197

Keywords: PPh3; NBS; triethylamine trihydrofluoride

酸フルオリド合成に関する論文のようです。カルボン酸から温和な反応条件で合成でき、容易に入手できるフッ素源を利用でき、生成物の取り出しもシンプルであることが、この合成法の売りのようです。


フッ素源はトリエチルアミン三フッ化水素酸塩[3HF·N(C2H5)3)]。単純なフッ化水素でも進む反応なのかもしれませんが、安全性やそのほかの理由でこの化合物が選ばれたのでしょう。Graphical Abstract中のNBSはN-ブロモコハク酸イミド。


光延反応と共通するところがあるのかもしれませんが、反応機構、特にカルボン酸のカルボキシル基がホスフィンとどのように反応するのか気になるので、読みたい論文に追加です。


この記事を書いた人
「牧岡ふうふ堂」オーナー。博士(工学)。
酒都圏在住。
某地方の国立系工業大学でアシスタントをしていました。 専門は有機反応・金属錯体(主に希土類)・π共役系。
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1949年はこんな年

人名反応など
Baileyペプチド合成Cope反応 [Doi 1]
Cornforth転位 [Doi 1]
ノーベル化学賞
化学熱力学への貢献、特に極低温における物性の研究
(William Francis Giauque)
できごと
スポーツニッポン創刊
東京理科大学設立
海王星の衛星ネレイドが発見される
東京、大阪、名古屋の3証券取引所が取引再開
通商産業省(経済産業省)発足
国立学校設置法施行(新制大学)
世界初のジェット旅客機初飛行(デ・ハビランド DH.106 コメット)
五円硬貨発行
大日本麦酒が朝日麦酒(アサヒビール)と日本麦酒(サッポロビール)に分割
鐘淵化学工業が発足
和江商事(ワコール)設立
湯川秀樹がノーベル物理学賞を受賞
サザエさん連載開始
京阪電気鉄道再発足
初のお年玉付年賀はがき販売

 

きょうのどうぶつ

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朝青龍の猫らしからぬ顔。

 

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