Blog

Selective Transformation of Strychnine and 1,2-Disubstituted Benzenes by C–H Borylation

Yutaro Saito, Kotono Yamanoue, Yasutomo Segawa,* and Kenichiro Itami*

Chem 2020, DOI: 10.1016/j.chempr.2020.02.004

C–H functionalizations of complex molecules such as natural products, pharmaceuticals, and π-conjugated systems are at the heart of constructing and modifying organic molecules, whereby the selectivity and predictability are of the utmost importance. Herein, we report the highly C3-selective C–H borylation of strychnine along with olefin isomerization, catalyzed by an iridium complex with a diphosphine ligand. This method enabled us to rapidly produce 15 strychnine derivatives by using the corresponding C3-borylated and isomerized analog as the common synthetic intermediate. The present catalyst system was also generally effective for the C–H functionalization of unsymmetric 1,2-disubstituted benzene derivatives, including fused π-systems (xanthenes, fluorenes, naphthalenes, and anthracenes) and pharmaceuticals (Nifedipine), in which the C–H positions furthest away from the bulky groups were borylated with high selectivity.

Related post

  1. All-benzene Carbon Nanocages: Si…
  2. Direct Arylation of Polycyclic A…
  3. Dragmacidin D Synthesis of Dragmacidin D via D…
  4. Palladium-catalyzed tetraallylat…
  5. Photo-induced arylation of carba…
  6. Manganese-Catalyzed Intermolecul…
  7. Six-fold C–H Borylation of Hexa-…
  8. Synthesis and Racemization Proce…

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