NEW INTRAMOLECULAR ALPHA-ARYLATION STRATEGY OF KETONES BY THE REACTION OF SILYL ENOL ETHERS TO PHOTOSENSITIZED ELECTRON-TRANSFER GENERATED ARENE RADICAL CATIONS - CONSTRUCTION OF BENZANNULATED AND BENZOSPIROANNULATED COMPOUNDS
G. Pandey et al., NEW INTRAMOLECULAR ALPHA-ARYLATION STRATEGY OF KETONES BY THE REACTION OF SILYL ENOL ETHERS TO PHOTOSENSITIZED ELECTRON-TRANSFER GENERATED ARENE RADICAL CATIONS - CONSTRUCTION OF BENZANNULATED AND BENZOSPIROANNULATED COMPOUNDS, Journal of organic chemistry, 63(9), 1998, pp. 2867-2872
Efficient intramolecular alpha-arylation of ketones is achieved by the
reaction of silyl enol ethers to photosensitized electron transfer (P
ET) generated arene radical cations. The arene radical cations are gen
erated by one-electron transfer from the excited state of the methoxy-
substituted arenes to ground-state 1,4-dicyanonaphthalene (DCN). This
arylation strategy has provided the unique opportunity of constructing
five- (23), six- (18), seven- (25) and eight-membered (27) benzannula
ted as well as benzospiroannulated (34) compounds. The explanation for
the formation of 27 has been advanced by considering the proximity be
tween the arene radical cation and silyl enol ether due to the self-co
iling in the aqueous environment.