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Beilstein J. Org. Chem. 2021, 17, 2959–2967, doi:10.3762/bjoc.17.205
Graphical Abstract
Figure 1: Redox potentials of representative nitrogenated HAT catalysts and photocatalysts [9-12,21-23].
Figure 2: Previous reports of DABCO as hydrogen abstractor in HAT reactions and this work.
Scheme 1: Aryl bromide and aldehyde scope. Isolated yields. aYield determined by 1H NMR analysis with 1,3-ben...
Scheme 2: Mechanistic investigations of the HAT reaction using DABCO.
Scheme 3: Proposed mechanism for aldehyde arylation. PC = photocatalyst Ir[dF(CF3)ppy]2(dtbbpy)PF6. SET = sin...
Figure 3: Free energy profile for the HAT step reactions between isovaleraldehyde with (top) DABCO and (botto...
Figure 4: TS structure for the HAT reaction between the DABCO radical cation and isovaleraldehyde obtained at...