Swann, Elizabeth published the artcileRates of reductive elimination of substituted nitrophenols from the (indol-3-yl)methyl position of indolequinones, Recommanded Product: 5-Methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione, the publication is Journal of the Chemical Society, Perkin Transactions 2 (2001), 1340-1345, database is CAplus.
A series of indolequinones bearing substituted nitrophenols on the (indol-3-yl)methyl position (I;R1,R2,R3,R4,R5 given: H,NO2,H,NO2,H; H,MeO,H,H,NO2;H,MeO,H,NO2,H; Me,F,H,NO2,H; H,CHO,H,NO2,H; etc. )was synthesized. The nitrophenol leaving groups were appropriately substituted to give a wide range (4 units) in phenolic pKa value. The rate of reductive elimination of phenoxide anions from the (indol-3-yl)methyl position of semiquinone radicals was dependent upon this pKa, with a decrease in 3.8 pK units shortening the half-life from 28 to 1.5 ms. Only 2,4-dinitrophenol (pKa = 3.9) was eliminated from an unsubstituted (indol-3-yl)methyl position at a rate that would compete with reoxidation of the radical by oxygen. A nitrothiophenol leaving group was eliminated comparatively slowly and only from the hydroquinone. These studies demonstrate the dependence upon leaving group pKa of the rate of reductive elimination from the (indol-3-yl)methyl position of indolequinones.
Journal of the Chemical Society, Perkin Transactions 2 published new progress about 192820-78-3. 192820-78-3 belongs to indole-building-block, auxiliary class Fused/Partially Saturated Cycles,Dihydroindoles, name is 5-Methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione, and the molecular formula is C13H17BO2, Recommanded Product: 5-Methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione.
Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles