Solvent-controlled leaving-group selectivity in aromatic nucleophilic substitution.
A solvent-controlled inversion of leaving group ability allows selective access to either of two internal substitution products in S(N)Ar reactions of substrates with competing leaving groups. Application of this principle in a selective synthesis of the highly functionalized xanthone core of the antibiotic FD-594 is presented.
Hintermann
Lukas
L
Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan.
Masuo
Ritsuki
R
Suzuki
Keisuke
K