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COMMUNICATION
Journal Name
and a fac-IVIr(ppy)3 complex. Once
, which
engages in 5-exo-trig cyclization to yield the radical
to afford the radical anion
Ⅰ
Commun., 2012, 48, 8799.
DOI: 10.1039/C9CC09876C
radical
Ⅱ is generated, its addition to 1a produces Ⅲ
3
4
5
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intermediate
Alternatively,
Ⅳ
Ⅳ
. At this point, two new C−C bonds are built.
undergoes a facile single-electron oxidation to
deliver carbocation
Finally, intermediate
Ⅴ
, which closes the photocatalytic cycle.
is trapped by the bromine anion,
Ⅴ
6
7
F. Rivas, T. Ling, Org. Prep. Proced. Int., 2016, 48, 254.
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8
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Figure 2 Plausible reaction mechanism.
In summary, we have developed
a novel one-step
photoredox catalytic ATRC-type synthesis of 4-bromo-3,3-
dialkyl-octahydro-indol-2-one scaffold which contains four
contiguous stereocenters. This synthesis was achieved under
mild conditions, and the reaction features high efficiency and
good functional group compatibility.
We are grateful to the NSFC (Grants 21632003, 21871116,
and 21572087), the Key Program of Gansu Province (Grant
17ZD2GC011), and the “111” Program from the MOE of P. R.
China for financial support.
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Sekine, M. Rudolph, and A. S. K. Hashmi, Chem. Commun.,
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9
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Conflicts of interest
The authors declare no conflict of interest.
Notes and references
14 For extensive optimization studies, see the Supporting
Information.
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4 | J. Name., 2012, 00, 1-3
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