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. Author manuscript; available in PMC: 2016 Oct 14.
Published in final edited form as: J Am Chem Soc. 2015 Oct 6;137(40):12796–12799. doi: 10.1021/jacs.5b09099

Table 1.

Optimization of Pt-Catalyzed C–H Hydroxylation of Protonated Dipropylamine

graphic file with name nihms748513t1.jpg
entry equiv
amine		 oxidant temp
(° C)		 K2PtCl4
loading
(mol
%)		 yield of 1 +
1aa 		1 : 1aa
1b 2 K2PtCl6 120 10 36% >10 : 1
2b 2 CuCl2 120 10 66% >10 : 1
3c 2 CuCl2 150 10 63% >10 : 1
4c 2 CuCl2 150 1 40% >10 : 1
5b 2 CuCl2 150 1 70% 8 : 1
6c 5 CuCl2 150 1 97% 8 : 1
7c 5 ---- 150 1 nde ----
8 c 5 CuCl2 150 ---- nde ----
9 c,d 5 CuCl2 150 1 <1% ----
a

Yield and ratio of products determined by 1H NMR. Reactions were conducted in sealed vials under an atmosphere of ambient air. Yields are calculated based on the oxidant (K2PtCl6 or CuCl2) as the limiting reagent.

b

48 h.

c

30 h.

d

No H2SO4 added.

e

Products 1 and 1a were not detected.