Tandem organocatalysis and photocatalysis: an anthraquinone-catalyzed indole-C3-alkylation/photooxidation/1,2-shift sequence.
Quinones exhibit orthogonal ground- and excited-state reactivities and are therefore highly suitable organocatalysts for the development of sequential catalytic processes. Herein, the discovery of an anthraquinone-catalyzed thermal indole-C3-alkylation with benzylamines is described, which can be combined sequentially with a new visible-light-driven catalytic photooxidation/1,2-shift reaction. The one-flask tandem process converts indoles into 3-benzylindole intermediates, which are further transformed into new fluorescent 2,2-disubstituted indoline-3-one derivatives.
Department of Chemistry/Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg (Germany).
Stephanie
S
Lerch
Lisa-Natascha
LN
Unkel
Malte
M
Brasholz
indoles; organocatalysis; photocatalysis; quinones; tandem catalysis