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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 2.

Intermolecular Hydroamination of Alkenes with 1 (0.4 M) Catalyzed by a Mixture of (L)AuCl (5 mol %) (L = 2a, 2b) and AgSbF6 (5 mol %) in Dioxane at 100 °C.

entry alkene alkene amt product L time (h) yield (%)a
graphic file with name nihms-106298-t0007.jpg graphic file with name nihms-106298-t0008.jpg
1 R = H 60 psi b 3 2b 24 99
2 R = Me 120 psi 2b 24 98
3 R = Et 120 psi 2b 24 96
4 R = (CH2)5CH3 10 equiv 2b 24 96
5 R = (CH2)3OH 10 equiv 2b 24 98
6 R = (CH2)3OBn 10 equiv 2b 40 95
7 R = (CH2)2CO2H 10 equiv 2a 40 98
8 R = (CH2)4CO2Et 10 equiv 2a 40 90
9 R = Ph 15 equiv 2b 36 75
10 graphic file with name nihms-106298-t0009.jpg 120 psic graphic file with name nihms-106298-t0010.jpg 2a 48 72
11 graphic file with name nihms-106298-t0011.jpg 20 equivc graphic file with name nihms-106298-t0012.jpg 2b 70 86d
a

Yield of isolated, regiochemically pure material of >95% chemical purity.

b

Reaction temperature = 60 °C.

c

Catalyst loading = 10 mol %.

d

Single diastereomer formed, relative configuration not determined.