Table 1. Scope of the catalytic diamination of 2-allylanilines^a.

Entry	Substrate	RNH2	Product	% Yield
1	1a, X = H, R1 = Ms,	TsNH2	2a	84 (75)b
2	1a	MsNH2	2b	69
3	1a	SESNH2	2c	80
4	1a	BzNH2	2d	50
5	1b, X = H, R1 = Ts	TsNH2	2e	64c
6	1c, X = H, R1 = SO2Bn	TsNH2	2f	65
7	1d, X = H, R1 = SO2C3H5	TsNH2	2g	75
8	1e, X = H, R1 = 3,5-di-t-Bu- 4-MeOC6H2SO2	TsNH2	2b, Ar = 3,5-di-t-Bu-4-MeOC6H2	84
9	1e	SESNH2	2i	77
10	1f, X = OMe, R1 = 3,5-di-t-Bu- 4-MeOC6H2SO2	TsNH2	2j	75
11	1g, X = Br, R1 = 3,5-di-t-Bu- 4-MeOC6H2SO2	TsNH2	2k	68
12	1h, X = Cl, R1 = 3,5-di-t-Bu- 4-MeOC6H2SO2	TsNH2	2l	70
13	1i, X = F, R1 = 3,5-di-t-Bu- 4-MeOC6H2SO2	TsNH2	2m	70
14	1j, X = Me, R1 = 3,5-di-t-Bu- 4-MeOC6H2SO2	TsNH2	2n	80
15d	1k	TsNH2	2o, 2p (dr = 58:42)	76
16d	1l	--	2q	73

Conditions:

^a20 mol % Cu(2-ethylhexanoate)₂, MnO₂ (3 equiv), 2,6-di-t-Bu-4-Me-pyridine (1 equiv), PhCF₃, RNH₂ (2.2 equiv), 110 °C, 24 h.

^bUsing 2 equiv (t-BuO)₂ at 100 °C instead of MnO₂.

^c31% of sultam 3 also isolated.

^dIn entry 15, [Cu(bisoxazoline)](OTf)₂ was used. For entry 16 [Cu(R,R)-Ph-box](OTf)₂ was used. 8% KMnO₄ and 1:1 PhCF₃:1,2-dichloroethane solvent were used in both reactions. Entries 1-3 (except 1^b) were taken from ref. 21.