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13 The slow reaction rates observed in 2c, 2l and 2m is
rationalized that fast back electron transfer from a radical
© 2023 The Author(s). Published by the Royal Society of Chemistry
Chemical Science
14
15
16
17
anion of a-ketoacylphosphonium to a radical cation of
aniline moiety would inhibit the following C–O bond
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We estimated that the preferential formation of 5y over 5y′
could be rationalized by the different rate of back electron
transfer on the radical ion pair. Based on the mechanism
involving charge transfer (Fig. 1B, bottom), single electron
transfer from more electron rich p-anisole moiety to aketoacylphosphonim moiety preferentially occurs to form
the radical ion. In the radical ion species, back electron
transfer from a-ketoacylphosphonim radical anion to the
p-anisole radical cation might be fast because the
corresponding electron transfer would be placed in the
vertex of Marcus’s parabola. This is same phenomenon
discussed in note 13. In contrast, back electron transfer
from radical cations of phenyl ring would be slow enough
to complete C–O bond formation of the radical ion
species. Therefore, 5y would be obtained as a major product.
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