Department of Biomolecular Engineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, Yokohama, Kanagawa 226-8501 Japan.
Org Lett. 2011 Sep 16;13(18):4873-5. doi: 10.1021/ol201952b. Epub 2011 Aug 15.
Nucleophilic addition of sulfonamides to 1-bromo-1-alkynes provided (Z)-N-(1-bromo-1-alken-2-yl)-p-toluenesulfonamides in good yield and in a highly regio- and stereoselective manner. Treatment of product (Z)-N-(1-bromo-1-octen-2-yl)-N-allyl-p-toluenesulfonamide with a palladium catalyst under Heck conditions afforded 1-(p-toluenesulfonyl)-2-hexyl-4-methylpyrrole in good yield. Other pyrroles with various substituents can also be prepared in good yield by this method.
磺酰胺的亲核加成反应可使 1-溴-1-炔烃高区域和立体选择性地得到（Z）-N-（1-溴-1-烯-2-基）-对甲苯磺酰胺。在钯催化剂存在下，通过 Heck 条件处理产物（Z）-N-（1-溴-1-辛烯-2-基）-N-烯丙基-对甲苯磺酰胺可得到高产率的 1-（对甲苯磺酰基）-2-己基-4-甲基吡咯。通过该方法还可以高产率制备具有各种取代基的其他吡咯。
