Department of Chemistry and Research Institute for Natural Sciences, Hanyang University, Seoul 133-791, Korea.
Org Lett. 2011 May 6;13(9):2228-31. doi: 10.1021/ol200481u. Epub 2011 Mar 29.
An NHC-catalyzed, regio- and stereoselective oxidative cyclization of o-alkynylbenzaldehydes bearing an unactivated alkyne moiety as an internal electrophile has been developed to afford phthalides and isocoumarins. A single organocatalytic system enabled two sequential C-O bond formations to take place in an atom economical manner via highly efficient dual activation. Molecular oxygen in air could be utilized as a source of an oxygen atom for the oxidation of aldehydes to the corresponding benzoic acids under our newly developed reagent system.
一种 NHC 催化的、区域和立体选择性的氧化环化反应，涉及带有未活化炔基部分的邻炔基苯甲醛作为内部亲电试剂，可得到邻苯二甲酸酐和异香豆素。通过高效的双重活化，一个单一的有机催化体系能够以原子经济的方式发生两个连续的 C-O 键形成。在我们新开发的试剂体系下，空气中的氧气可以作为氧化醛为相应苯甲酸的氧原子来源。
