36977-36-3Relevant academic research and scientific papers
Oxidative cross-coupling of allenyl ketones and organoboronic acids: Expeditious synthesis of highly substituted furans
Xia, Ying,Xia, Yamu,Ge, Rui,Liu, Zhen,Xiao, Qing,Zhang, Yan,Wang, Jianbo
, p. 3917 - 3921 (2014)
Allenyl ketones are employed as coupling partners in palladium-catalyzed oxidative cross-coupling reactions with organoboronic acids. This reaction constitutes an efficient methodology for the synthesis of highly substituted furan derivatives. Palladium-carbene migratory insertion is proposed as the key step in this transformation. Migration patterns: Allenyl ketones are employed as a coupling partner in a palladium-catalyzed oxidative cross-coupling reaction with organoboronic acids. This reaction constitutes an efficient methodology for the synthesis of highly substituted furan derivatives. Palladium-carbene migratory insertion is proposed as the key step in this transformation. BQ=1,4-benzoquinone.
An expedient route to substituted furans via olefin cross-metathesis
Donohoe, Timothy J.,Bower, John F.
supporting information; experimental part, p. 3373 - 3376 (2010/08/05)
The olefin cross-metathesis (CM) reaction is used extensively in organic chemistry and represents a powerful method for the selective synthesis of differentially substituted alkene products. Surprisingly, efforts to integrate this remarkable process into strategies for aromatic and heteroaromatic construction have not been reported. Such structures represent key elements of the majority of small molecule drug compounds; methods for the controlled preparation of highly substituted derivatives are essential to medicinal chemistry. Here we show that the olefin CM reaction, in combination with an acid cocatalyst or subsequent Heck arylation, provides a concise and flexible entry to 2,5-di- or 2,3,5-tri-substituted furans. These cascade processes portend further opportunities for the regiocontrolled preparation of other highly substituted aromatic and heteroaromatic classes.
