TABLE 1.

Carboamination of γ-(N-Arylamino)alkenes with Aryl Chlorides^a

entry	amine	product	regioselectivityb	yieldc
1	1a	2a	43:3:0:1	79%
2	1a	2b	38:3:0:1	74%
3	1a	2c	27:2:0:1	79%
4	1b	2d	10:1:0:0	66% (>20:1 dr)
5	1c	2e	>20:1	65% (>20:1 dr)d
6	1d	2f	11:1e	70% (>20:1 dr)f
7	1d	2g	12:1e	69% (>20:1 dr)f

^aConditions: amine (1.0 equiv), aryl chloride (1.1–1.4 equiv), NaO^tBu (1.2 equiv), Pd₂(dba)₃ (1 mol %), PCy₂Ph (4 mol %), toluene (0.25 M), 110 °C.

^bDetermined by GC and GC/MS analysis. The minor regioisomers formed are analogous to 3–5 shown in eq 1.

^cIsolated yield (average of two or more experiments).

^dPCy₃•HBF₄ was used in place of PCy₂Ph.

^eThe minor regioisomer was arylated at C4 rather than C5.

^fP(^tBu)₂Me•HBF₄ was used in place of PCy₂Ph.