Catalytic cross-coupling reaction of esters with organoboron compounds and decarbonylative reduction of esters with HCOONH4: A new route to acyl transition metal complexes through the cleavage of acyl-oxygen bonds in esters

Hiroto Tatamidani, Kazuhiko Yokota, Fumitoshi Kakiuchi, Naoto Chatani

研究成果: Article査読

91 被引用数 (Scopus)

抄録

The Ru3(CO)12-catalyed cross-coupling reaction of esters with organoboron compounds leading to ketones is described. A wide variety of functional groups can be tolerated under the reaction conditions. Aromatic boronates function as a coupling partner to give aryl ketones. Acyl-alkyl coupling to dialkyl ketones is also achieved by the use of 9-alkyl-9-BBN in place of boronates. The Ru3(CO)12- catalyzed decarbonylative reduction of esters with ammonium formate (HCOONH 4) leading to hydrocarbons is also described. No expected aldehydes are produced, and controlled experiments indicate that aldehydes are not intermediate for the transformation. A hydrosilane can also be used as a reducing reagent in place of HCOONH4. A wide variety of functional groups are compatible for both reactions. The key step for both catalytic reactions is the directing group-promoted cleavage of an acyl carbon-oxygen bond in esters, leading to the generation of acyl transition metal alkoxo complexes.

本文言語English
ページ(範囲)5615-5621
ページ数7
ジャーナルJournal of Organic Chemistry
69
17
DOI
出版ステータスPublished - 2004 8 20
外部発表はい

ASJC Scopus subject areas

  • 有機化学

フィンガープリント

「Catalytic cross-coupling reaction of esters with organoboron compounds and decarbonylative reduction of esters with HCOONH<sub>4</sub>: A new route to acyl transition metal complexes through the cleavage of acyl-oxygen bonds in esters」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

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