In situ anionic shielding for regioselective metalation: directed peri and iterative metalation routes to polyfunctionalized 7-azaindoles.
Strolling the ring: a general regioselective directed peri(C4)-metalation route to 1 through an in situ N-anionic protection of C2 is reported. The azaindoles may be elaborated by directed ortho metalation (DoM) and Suzuki coupling to more complex heterocyclic systems. An iterative ring-walk DoM sequence furnishes the exhaustively substituted 2. DMG=directed metalation group, TMEDA=N,N,N',N'-tetramethylethylenediamine, TMS=trimethylsilyl.
Department of Chemistry, Queen's University, Kingston, Ontario, Canada.
Cédric
C
Schneider
Emilie
E
David
Anton A
AA
Toutov
Victor
V
Snieckus