Reduction of arenediazonium salts by tetrakis(dimethylamino)ethylene (TDAE): efficient formation of products derived from aryl radicals.
Tetrakis(dimethylamino)ethylene (TDAE 1), has been exploited for the first time as a mild reagent for the reduction of arenediazonium salts to aryl radical intermediates through a single electron transfer (SET) pathway. Cyclization of the aryl radicals produced in this way led, in appropriate substrates, to syntheses of indolines and indoles. Cascade radical cyclizations of aryl radicals derived from arenediazonium salts are also reported. The relative ease of removal of the oxidized by-products of TDAE from the reaction mixture makes the methodology synthetically attractive.
Mahesh
Mohan
M
WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295, Cathedral Street, Glasgow G1 1XL, UK.
Murphy
John A
JA
LeStrat
Franck
F
Wessel
Hans Peter
HP