Blog

Mechanistic Studies on the Pd-catalyzed Direct C-H Arylation of 2-Substituted Thiophene Derivatives with Arylpalladium Bipyridyl Complexes

Marc Steinmetz, Kirika Ueda, Stefan Grimme, Junichiro Yamaguchi, Sylvia Kirchberg, Kenichiro Itami, and Armido Studer

Chem. Asian J. 2012, Early View. DOI: 10.1002/asia.201101011

 

Direct C–H phenylation of 2-ethylthiophene and 2-chlorothiophene with PhPdI(bipy) complex to form either the corresponding 4-phenyl or 5-phenylthiophene derivative is studied under stoichiometric conditions using various Lewis acids as additives. It is shown that reactions occur via the corresponding cationic Pd complex (PhPdbipy+) and that the counteranion determines the regioselectivity. High-level DFT calculations reveal that C–C bond formation occurs via a carbopalladation pathway and not via electrophilic palladation. These calculations give some indications regarding the regioselectivity of the thiophene arylation.

 

Related post

  1. Cycloparaphenylene-Based Ionic D…
  2. Selective Synthesis of [12]Cyclo…
  3. Combined experimental and theore…
  4. Design and Synthesis of Carbon N…
  5. N-doped Nonalternant Aromatic Be…
  6. Recent advances in acetylene-bas…
  7. Synthesis of Cycloiptycenes from…
  8. Regioselective Unsymmetrical Tet…

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