Rapid route to 3,4-substituted indoles via a directed ortho metalation-retro-Mannich sequence.
[reaction: see text] In the presence of NXS (X = Br, I, Cl), gramine derivatives 1, derived by combined directed ortho metalation (DoM)-cross-coupling sequences, rapidly undergo retro-Mannich fragmentation (2) to afford 3-halo indoles 3 in 37-88% yields.
Chauder, Brian,Larkin, Andrew,Snieckus, Victor
p. 815 - 817
(2007/10/03)
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