Synthesis of Fused‐Pyrazines via Palladium‐Catalyzed Double Benzyl Isocyanide Insertion and Cross‐Dehydrogenative Coupling

作者：Gopal Chandru Senadi, Bing‐Chun Guo, Yu‐Ching Chang, Wan‐Ping Hu, Jeh‐Jeng Wang · 发表于：Advanced Synthesis & Catalysis · 年份：2017 · DOI：10.1002/adsc.201701202 · 被引用次数：25 · 研究领域：Catalytic C–H Functionalization Methods、Catalytic Cross-Coupling Reactions、Synthesis and Catalytic Reactions

Abstract A palladium‐catalyzed cascade reaction has been realized for the synthesis of 5 H ‐pyrrolo[2,3‐ b ]pyrazines and 5 H ‐pyrazino[2,3‐ b ]indoles from benzyl isocyanide by choosing o ‐pivaloyloximes or o ‐iodoanilines as a suitable substrate. The key steps involved are (i) oxidative addition of palladium through N–O or C–I cleavage; (ii) migratory double isocyanide insertion; and (iii) cross‐dehydrogenative coupling. Notable features are good functional group tolerance as well as formation of three C–C and one C–N bonds. magnified image