Department of Chemistry , University of Minnesota , 207 Pleasant Street SE, Minneapolis , Minnesota 55455 , United States.
Org Lett. 2018 Nov 16;20(22):7145-7148. doi: 10.1021/acs.orglett.8b03085. Epub 2018 Nov 5.
Reactions of tethered, tertiary sulfonamides with thermally generated benzynes are reported. Typically, the N-S bonds in the substrates cleave, and saturated heterocycles [tetrahydroquinolines ( n = 2) and indolines ( n = 1)] are formed. The process is accompanied by either sulfonyl transfer or desulfonylation from a zwitterionic intermediate, with the favored pathway being largely dependent upon the size (5- vs 6-membered) of the N-containing ring in the zwitterion.
本文报道了偕位三级磺酰胺与热生成苯炔的反应。通常，底物中的 N-S 键断裂，形成饱和杂环[四氢喹啉（n=2）和吲哚啉（n=1）]。该过程伴随着由两性离子中间体进行的磺酰基转移或脱磺酰基反应，其中有利的途径在很大程度上取决于两性离子中环中含氮原子的大小（5- 或 6- 元环）。
