Blog

One-Step Annulative π-Extension of Alkynes with Dibenzosiloles or Dibenzogermoles by Palladium/o-chloranil Catalysis

Kyohei Ozaki, Keiichiro Murai, Wataru Matsuoka, Katsuaki Kawasumi, Hideto Ito,* and Kenichiro Itami*

Angew. Chem. Int. Ed. 201655, 1361–1364. DOI: 10.1002/anie.201610374

 Reliable and short synthetic routes to polycyclic aromatic hydrocarbons and nanographenes are important in materials science. Herein, we report an efficient one-step annulative π-extension reaction of alkynes that provides access to diarylphenanthrenes and related nanographene precursors. In the presence of a cationic palladium/o-chloranil catalyst system and dibenzosiloles or dibenzogermoles as π-extending agents, a variety of diarylacetylenes are transformed successfully into 9,10-diarylphenanthrenes in a single step with good functional-group tolerance. Furthermore, double π-extension reactions of 1,4-bis(phenylethynyl)benzene and diphenyl-1,3-butadiyne are demonstrated, affording oligoarylene products, which show potential for application in the synthesis of larger polycyclic aromatic hydrocarbons and nanographenes.

Related post

  1. tert-Butoxide-Mediated C-H Bond …
  2. Synthesis of a zigzag carbon nan…
  3. Nickel-Catalyzed C-H Arylation o…
  4. 2,4- and 2,5-Disubstituted Arylt…
  5. Annulative π-Extension (APEX): A…
  6. Probing strigolactone receptors …
  7. One-step synthesis to polycyclic…
  8. Synthesis of a Möbius carbon nan…

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