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. Author manuscript; available in PMC: 2010 Jun 24.
Published in final edited form as: J Am Chem Soc. 2009 Apr 22;131(15):5372–5373. doi: 10.1021/ja9001162

Table 1.

Intermolecular Hydroamination of Alkenes (120 psi) with Cyclic Ureas Catalyzed by a Mixture of (2a)AuCl (5 mol %) and AgOTf (5 mol %) in Dioxane at 100 °C.

entry nucleophile alkene product time (h) yielda
graphic file with name nihms-106298-t0001.jpg graphic file with name nihms-106298-t0002.jpg graphic file with name nihms-106298-t0003.jpg
1 X = NMe (1) R = H 3 20 99
2 R = Me 62 97
3b R = Et 69 99
4 R = (CH2)5Me 24 38c
5 X = Nt-Bu R = H 40 80
6 X = O R = H 72 75
graphic file with name nihms-106298-t0004.jpg graphic file with name nihms-106298-t0005.jpg graphic file with name nihms-106298-t0006.jpg
7 n = 1 R = H 20 95
8 b n = 1 R = Me 65 85
9 n = 1 R = Et 68 86d
10 b n = 2 R = H 19 98
11 n = 2 R = Me 67 86
a

Isolated yield of >95% purity.

b

Catalyst loading = 10 mol %.

c

GC yield. 1-Octene loading = 10 equiv.

d

dr = 1:1.