6533b850fe1ef96bd12a8170

RESEARCH PRODUCT

ChemInform Abstract: Regioselective Proton-Catalyzed Diarylmethylation of Indoles with 9H-Xanthydrol, Dibenzosuberenol, and Bis(4-dimethylaminophenyl)methanol.

Ulf PindurRainer Deschner

subject

Indole testchemistry.chemical_compoundProtonchemistryElectrophileRegioselectivityGeneral MedicineMethanolXanthydrolMedicinal chemistryCatalysis

description

3-Isopropylindole (4) is xanthenylated both at N-1 (stereocontrolled major reaction), C-2, and on the phenyl nucleus of the indole skeleton by xanthydrol (1). Other carbinols such as dibenzosuberenol (2) and bis[4-dimethylaminophenyl]methanol (3) with lower electrophilic SN1 activities than 1 do not react with 4 but do react very selectively with simple methylindoles to form diarylmethylated derivatives.

https://doi.org/10.1002/chin.198911174