Table 3.

Substrate Scope of Pt-Catalyzed C-H Hydroxylation of Secondary and Tertiary Amines^a

entry	major product	isolated yield	isolated selectivity (crude selectivity)
1		87%	>20 : 1 (8 : 1)
2		76%	7 : 1 (5 : 1)
3		47%	>10 : 1 (3 : 1)
4		54%	>20 : 1 (8 : 1)
5		46%	>20 : 1 (>20 : 1)
6b		65%	>10 : 1 (5 : 1)
7c		88%	>20 : 1 (>20 : 1)
8d		102%	>20 : 1 (7 : 1)
9e		90%	>20 : 1 (14 : 1)
10e		122%	>20 : 1 (10 : 1)
11f		<5%g	----
12f		<5%g	----

^aGeneral conditions: 1 mol % K₂PtCl₄, 1 equiv CuCl₂, 5 equiv of amine, 5.5 equiv H₂SO₄ (1.1 equiv relative to amine), 150 °C, 24 h.

^bEntry 6: Amine used as HCl salt, 10 mol % K₂PtCl₄.

^cEntry 7: 15 equiv amine, 16.5 equiv H₂SO₄, 48 h.

^dEntry 8: 0.5 mol % K₂PtCl₄, 15 equiv amine, 16.5 equiv H₂SO₄.

^eEntries 9–11: 5 mol % K₂PtCl₄.

^fEntries 11–12: amine used as HCl salt, 10 mol % K₂PtCl₄;

^gYields estimated by ¹H NMR analysis of crude reaction mixtures; <5% of C(sp³)–H hydroxylation or C(sp³)–H chlorination products were observed.