The regioselective synthesis of both 2- and 3-alkoxyindoles from a common intermediate, 2-alkoxy-3-bromoindolines (ROBIN), is described. The 2-alkoxyindoles are obtained by a base-promoted regioselective elimination of HBr from ROBIN, whereas the synthesis of 3-alkoxyindoles is achieved by a silver-mediated alkoxylation followed by an acid-promoted elimination of alkoxide. This key elimination features the complete regioselectivity and no need for catalysts, that makes it have potential synthetic applications. Furthermore, this protocol is user friendly because ROBIN is able to be prepared from commercially available indoles and is a bench-stable easy-to-handle crystalline substrate, thus allowing the concise synthesis of a variety of both 2- and 3-alkoxyindoles.

中文翻译：

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回顾2-烷氧基-3-溴二氢吲哚：烷氧基吲哚的区域选择性合成的对照C-2对C-3消除。

描述了从共同的中间体2-烷氧基-3-溴吲哚啉（ROBIN）中2-和3-烷氧基吲哚的区域选择性合成。2-烷氧基吲哚是通过从ROBIN碱促进的区域选择性去除HBr而获得的，而3-烷氧基吲哚的合成是通过银介导的烷氧基化反应，然后是酸促进的醇盐消除。这种关键的消除方法具有完全的区域选择性，并且不需要催化剂，使其具有潜在的合成应用。此外，该协议是用户友好的，因为ROBIN可以从市售的吲哚制备，并且是板凳稳定且易于处理的晶体底物，因此可以简洁地合成各种2-和3-烷氧基吲哚。