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Synthesis of Fused‐Pyrazines via Palladium‐Catalyzed Double Benzyl Isocyanide Insertion and Cross‐Dehydrogenative Coupling
Author(s) -
Senadi Gopal Chandru,
Guo BingChun,
Chang YuChing,
Hu WanPing,
Wang JehJeng
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701202
Subject(s) - chemistry , isocyanide , palladium , catalysis , cleavage (geology) , bond cleavage , combinatorial chemistry , migratory insertion , stereochemistry , functional group , medicinal chemistry , organic chemistry , fracture (geology) , engineering , polymer , geotechnical engineering
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.