Blog

Decarbonylative organoboron cross-coupling of esters by nickel catalysis


Kei Muto, Junichiro Yamaguchi, Djamaladdin G. Musaev and Kenichiro Itami

Nature Commun. 2015, 6, 7508. DOI: 10.1038/ncomms8508

The Suzuki–Miyaura cross-coupling is a metal-catalysed reaction in which boron-based nucleophiles and halide-based electrophiles are reacted to form a single molecule. This is one of the most reliable tools in synthetic chemistry, and is extensively used in the synthesis of pharmaceuticals, agrochemicals and organic materials. Herein, we report a significant advance in the choice of electrophilic coupling partner in this reaction. With a user-friendly and inexpensive nickel catalyst, a range of phenyl esters of aromatic, heteroaromatic and aliphatic carboxylic acids react with boronic acids in a decarbonylative manner. Overall, phenyl ester moieties function as leaving groups. Theoretical calculations uncovered key mechanistic features of this unusual decarbonylative coupling. Since extraordinary numbers of ester-containing molecules are available both commercially and synthetically, this new ‘ester’ cross-coupling should find significant use in synthetic chemistry as an alternative to the standard halide-based Suzuki–Miyaura coupling.

Related post

  1. Iridium Catalysis for C-H Bond A…
  2. C-H Activation Enables Rapid Str…
  3. Synthesis of Cycloiptycenes from…
  4. Electro-Activated Conductivity a…
  5. (日本語) Direct Coupling of Naphtha…
  6. C–H Functionalization of Azines
  7. Synthesis, Structure, and Electr…
  8. Synthesis, Properties, and Packi…

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