Abstract
Reported is the synthesis of indolizines 3 via the copper(I)-catalyzed [3+2] cyclization of pyridines 1 with alkenyldiazoacetates 2. This method is tolerant of a wide range of sensitive functional groups due to the mild nature of the reaction conditions, although the yields are often moderate. Electron-rich pyridines (R¹ = OMe, NMe2) are unsuitable substrates, and 2-substituted pyridines also led to sluggish reactivity. Pyridines 1 bearing 3-substituents gave a mixture of products 3, with EWGs favoring 6-substitution and alkyl groups/halogens favoring 4-substituted products. Three examples of benzo-fused pyridine substrates 4-6 were also presented. A tentative mechanism is proposed supported by theoretical calculations.
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