Table 1.
Chemoselective Aziridination and C–H Amination of Homoallenic Carbamates Catalyzed by Silver Catalysts
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---|---|---|---|---|---|---|---|---|
entrya | catalystb,c |
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4a | 5a | entrye |
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4b | 5b |
1 | Rh2(esp)2 |
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35% | 17% | 9 |
![]() |
5% | 80% |
2 | AgOTf/phen |
![]() |
79% | --- | 10 |
![]() |
80% | 14% |
3 | AgOTf/bipy |
![]() |
60% | --- | 11 |
![]() |
68% | 11% |
4 | AgOTf/bathophen |
![]() |
57% | --- | 12 |
![]() |
84% | 12% |
5 | AgOTf/p-MeObipy |
![]() |
72% | --- | 13 |
![]() |
73% | 11% |
6 | AgOTf/dafone |
![]() |
32% | --- | 14 |
![]() |
59% | 22% |
7 | AgOTf/p-Ph-bipy |
![]() |
66% | --- | 15 |
![]() |
62% | 20% |
8 | AgOTf/terpy |
![]() |
27% | 35% | 16 |
![]() |
9% | 61% |
Substrate 3a.
5 mol % Rh2(esp)2, 2 equiv PhlO.
Ag: 20 mol % AgOTf, 25 mol % ligand, 2 equiv PhIO, 4 Å MS, CH2Cl2.
A: aziridination. I: insertion.
Substrate 3b.