Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Org Lett. 2010 Sep 3;12(17):3796-9. doi: 10.1021/ol101472k.
Addition of nitrosobenzene to pinacol allylboronates leads to oxidation of the organoboron with concomitant rearrangement of the substrate alkene. This reaction appears to proceed by allylboration of the nitroso group in analogy to carbonyl and imine allylation reactions. Remarkably, the N-O bond is cleaved during the reaction such that simple alcohols are the final reaction product.
亚硝基苯与频哪醇烯丙基硼酸酯加成导致有机硼的氧化,同时底物烯烃发生重排。该反应似乎通过亚硝基基团的烯丙基硼化反应进行,类似于羰基和亚胺的烯丙基化反应。值得注意的是,在反应过程中 N-O 键被切断,因此简单的醇是最终的反应产物。