Synthesis of 4-functionalized indoles via benzyne cyclization of N-(2- lithioallyl)-2-fluoroanilines

Article abstract of DOI:10.1016/S0040-4039(99)80109-9

Treatment of N-(2-bromoallyl)-N-methyl-2-fluoroaniline with tert- butyllithium affords 1,3-dimethyl-4-lithioindole, via intramolecular addition to a tethered benzyne intermediate. Further reaction with electrophiles leads to 4-functionalized 3-methylindol