Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal , C.P. 8888, Succ. Centre-Ville, Montréal, Québec H3C 3P8, Canada.
J Org Chem. 2017 Nov 17;82(22):11884-11890. doi: 10.1021/acs.joc.7b01595. Epub 2017 Aug 25.
Substituted anilines containing a sulfonyl group may be oxidized in situ in the presence of methanol and a hypervalent iodine reagent to form an active iminium species. Subsequent addition of phosphines or phosphites in the same pot produces meta-substituted anilines in good yields. This formal C-H bond functionalization is a direct and efficient means of selectively substituting the meta-position of anilines to produce aromatic phosphonium ions or phosphonates.
含有磺酰基的取代苯胺在甲醇和高价碘试剂存在下可以原位氧化，形成活性亚胺物种。随后在同一锅中加入膦或亚磷酸酯，可高产率得到间位取代苯胺。这种形式的 C-H 键官能化是一种直接有效的方法，可以选择性取代苯胺的间位，生成芳基磷鎓离子或磷酸酯。
