Blog

Catalytic Dehydrogenative C–H Imidation of Arenes Enabled by Photo-generated Hole Donation to Sulfonimide

Eri Ito, Tomohiro Fukushima, Takahiro Kawakami, Kei Murakami,* Kenichiro Itami*

Chem 2017, 2, 383–392.

In view of the significance of arylamine derivatives in organic materials and pharmaceuticals, development of useful aromatic C–H amination has long been sought. Although many attempts have been made to achieve dehydrogenative C–H amination, the low reactivity of simple arenes makes the equimolar amination as a challenging subject in synthetic chemistry. We report equimolar C–H/N–H coupling of arene and sulfonimide by dehydrogenative aromatic imidation. This was achieved by a ruthenium-based photoredox mediator using arenes as the limiting reagent. A wide range of arenes such as polycyclic aromatic hydrocarbons and heteroarenes as well as various sulfonimides were applicable to the reaction. This electrochemistry-based mechanistic study revealed that the coupling reaction is initiated by oxidation of sulfonimide with ruthenium catalyst.

Related post

  1. Fe-Catalyzed Oxidative Coupling …
  2. Palladium-Catalyzed C-H Activati…
  3. Phenanthro[9,10-a]corannulene by…
  4. Helically Twisted Tetracene: Syn…
  5. Late-Stage C–H Coupling Enables …
  6. Nickel-Catalyzed C-H Arylation o…
  7. Macrocyclization by Rh-Catalyzed…
  8. C-H Arylation of Phenanthrene wi…

Twitter@Itami Lab

Itami Lab Facebook

Instagram@Itami Lab

最近の記事

Flickr@Itamilab

天池先輩からコーヒースープ伴夫妻からのお歳暮です!潤さん、宮村さん、ありがとうございます!!武藤さん、ビールありがとうございます!平賀大都わーいやなさん、あつしさん、ありがとうございます!!だいぶ前だけど、Stripes look #ootdHalloween lookラインを洗う時ですら格好良く。戸谷先生教育実習!imageけいしゅう、誕生日おめでとう!誕生日は英吉家!!3年生に名古屋ぼろ勝ちアピール中!!アリシア卒業おめでとう女子会!
PAGE TOP