Av isible light-mediated difluoroacetylation of cinnamamides with ethylb romodifluoroacetate as aC F 2 radical precursori sd escribed. Ther eaction incorporates tandem cyclization or cyclization/dearomatizationp rocesses.T he latter process occurs when there is a p-RO substituento nt he aniline.T hisp rotocola ffords straightforward new routes to separately synthesize quinoline-2-ones and spiro[4.5]decanes in moderate to good yields.
A novel visible light promoted carbodifluoroalkylation of allylic alcohols is disclosed. A series of difluoro 1,5-dicarbonyl compounds were obtained through a tandem radical addition and 1,2-aryl migration process. Mechanistic analysis indicated that the 1,2-aryl rearrangement proceeded via a radical intermediate.
The TBPB promoted tandem oxidative C(sp(3))-H bond functionalization of simple alkanes/alkylation-initiated dearomatization of N-phenyl-cinnamamides is reported, providing a direct method for the synthesis of alkylated 1-azaspiro[4.5]decanes with excellent regioselectivity and diastereoselectivity. The formation of two C(sp(3))-C(sp(3)) bonds and construction of a spirodienone motif are involved in one step.
A new synthetic strategy for C-C bond formation has been developed via a free radical cascade process under metal-free conditions. Activation of inert C(sp(3))-H/elimination of SO2/C-C bond formation were achieved in sequence in this system.
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