Table 1.

Catalytic Diamination of Disubstituted Terminal Olefins^a

entry	substrate 1	product 3	yield (%)d
1	1a, X = H		91
2	1b, X = o-F		47
3b	1c, X = o-OMe		50
4	1d, X = m-Br		86
5	1e, X = m-OMe		74
6	1f, X = m-Me		83
7	1g, X = m-CN		80
8	1h, X = p-Me		64
9	1i, X = p- Cl		90
10c	lj		86
11	1k, R = Me		71
12	1l, R = Ph		66
13b	1m, R = OMe		63
14	ln		55
15	1o, R = Ph		65
16	1p, R = Me		54

^aAll reactions were carried out with olefin (1) (0.4 mmol), di-tert-butyldiaziridinone (2) (0.8 mmol) (added by syringe pump over 8 h), CuCl-PPh₃ (1:1) (0.02 mmol) in CDCl₃ (0.3 mL) at 65 °C unless otherwise stated. Upon complete addition of 2, the reaction mixture was stirred at 65 °C for an additional time period (1 h for entries 1, 4, 5, 6, 8, and 9; 2 h for entries 7, 10, and 15; 4 h for entry 11; 7 h for entries 3, 12, 14, and 16; 10 h for entries 2 and 13).

^bCuCl-PPh₃ (1:1) (0.04 mmol) was used.

^cThe reaction was carried out with olefin (0.2 mmol), di-tert-butyldiaziridinone (2) (0.4 mmol), and CuCl-PPh₃ (1:1) (0.02 mmol) in CDCl₃ (0.3 mL).

^dIsolated yield based on olefin.