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. Author manuscript; available in PMC: 2015 Jul 6.
Published in final edited form as: J Am Chem Soc. 2013 Nov 11;135(46):17238–17241. doi: 10.1021/ja406654y

Table 1.

Chemoselective Aziridination and C–H Amination of Homoallenic Carbamates Catalyzed by Silver Catalysts

graphic file with name nihms702492u1.jpg
entrya catalystb,c graphic file with name nihms702492u2.jpgd 4a 5a entrye graphic file with name nihms702492u3.jpg 4b 5b
1 Rh2(esp)2 graphic file with name nihms702492t1.jpg 35% 17% 9 graphic file with name nihms702492t2.jpg 5% 80%
2 AgOTf/phen graphic file with name nihms702492t3.jpg 79% --- 10 graphic file with name nihms702492t4.jpg 80% 14%
3 AgOTf/bipy graphic file with name nihms702492t5.jpg 60% --- 11 graphic file with name nihms702492t6.jpg 68% 11%
4 AgOTf/bathophen graphic file with name nihms702492t7.jpg 57% --- 12 graphic file with name nihms702492t8.jpg 84% 12%
5 AgOTf/p-MeObipy graphic file with name nihms702492t9.jpg 72% --- 13 graphic file with name nihms702492t10.jpg 73% 11%
6 AgOTf/dafone graphic file with name nihms702492t11.jpg 32% --- 14 graphic file with name nihms702492t12.jpg 59% 22%
7 AgOTf/p-Ph-bipy graphic file with name nihms702492t13.jpg 66% --- 15 graphic file with name nihms702492t14.jpg 62% 20%
8 AgOTf/terpy graphic file with name nihms702492t15.jpg 27% 35% 16 graphic file with name nihms702492t16.jpg 9% 61%
a

Substrate 3a.

b

5 mol % Rh2(esp)2, 2 equiv PhlO.

c

Ag: 20 mol % AgOTf, 25 mol % ligand, 2 equiv PhIO, 4 Å MS, CH2Cl2.

d

A: aziridination. I: insertion.

e

Substrate 3b.