Viewed: 07:34:29 in April 10, 2020

One-pot fluorosulfurylation of Grignard reagents using sulfuryl fluoride (Lee, Cayo; Ball, Nicholas D.; Sammis, Glenn M.)
Chem. Commun. 2019, 55 (98), 14753−14756.

Keywords: Mg; SO₂F₂; THF; SPS; 読みたい論文シリーズ; 有機化学; ブログ

有機マグネシウム反応剤(Grignard反応剤)とフッ化スルフリルの反応について報告している論文のようです。

単純に考えれば生成物はフッ化スルホニルですが、フッ化スルホニルには硫黄−フッ素結合がありますので、こことさらに有機マグネシウムが反応してスルホンになるし、アルコールやアミンと反応させればスルホン酸エステルやスルホン酸アミドになる、と。なるほど。

有機マグネシウムの反応について確認しておきたいことの一つが「どっちがどっちに」というやつです。容器(最近はフラスコじゃない反応も多いです)に先に入っているのは有機マグネシウムかフッ化スルホニルか。ここはSupporing informationに大抵あって、この論文の反応ではフッ化スルホニルの入っている容器に有機マグネシウムを入れていくのがメインの模様。基質によってはどっちかわからんぞというのもありです。

あと反応溶媒については例えばTHFだと購入品とかガラスの蒸留器に溜めたものとかごっつい蒸留システムからとか、いろいろ試してあるのが面白いですね。

反応自体がシンプルなので本文の内容がある程度予想できますが、応用例とかあるかもしれないので、読みたい論文に追加です。

 

ここの画像を使用しています。

アゴ乗せチャシロさん。

 

Just finished the calculations: 2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG) https://t.co/j55DgLmIcC pic.twitter.com/gC09wlQE0v

— nanoniele (@nanoniele) December 6, 2019

 

　

 

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