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Tandem Palladium Catalysis for Rapid Construction of 3,4‐Fused Tricyclic Indoles
Author(s) -
Wang Weiyi,
Yang Min,
Han Dandan,
He Qiuqin,
Fan Renhua
Publication year - 2020
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.201901544
Subject(s) - chemistry , tandem , catalysis , palladium , intramolecular force , combinatorial chemistry , sodium formate , molecule , tricyclic , formate , organic chemistry , materials science , composite material
Tandem catalysis, the use of a single catalyst to promote two or more mechanistically distinct cycles in one pot to assemble complex organic molecules, is an attractive target. In this paper, we report a reductant‐triggered tandem palladium catalysis process that rapidly assembles 3,4‐fused tricyclic indoles from three readily available starting materials. This tandem process involves a Pd 0 ‐catalyzed in situ coupling/cyclization/Michael addition reaction to install simultaneously two functional groups at the C4 and the C3 positions of indoles. This is followed by a Pd 0 ‐catalyzed intramolecular cyclization which builds a seven‐membered C4, C3‐bridge. Sodium formate is used to trigger the necessary switching between the palladium catalysed reactions.