Table 1. Screening of conditions for benzylic Csp³–H arylation of N,N-dimethylbenzylamine ^a .

Entry	HAT cat.	P.C.	Time (h)	Yield b (%)	2a : 3a b
1 c	—	15	12	95	1 : 8.5
2	4	15	12	91	>20 : 1
3	4	15	1	93	>20 : 1
4	10	15	1	23	>20 : 1
5	11	15	1	43	>20 : 1
6	12	15	1	Trace	—
7	13	15	1	Trace	—
8	14	15	1	12	1 : 2
9	4	16	1	42	>20 : 1
10	4	17	1	No reaction
11 d , e	4	15	2	90 (87) f	>20 : 1
12 d , g	4	15	2	72	>20 : 1

^aThe reactions were run on 0.2 mmol scale.

^bYield and regioisomeric ratio were determined by ¹H NMR analysis using 1,1,2,2-tetrachloroethane as an internal standard.

^cData from Scheme 3.

^d1 mol% of PhC(O)SH and 0.5 mol% of Ir(ppy)₃ were used on a 1 mmol scale.

^e2 equiv. of N,N-dimethylbenzylamine was used.

^fIsolated yield.

^g1 equiv. of N,N-dimethylbenzylamine was used. P.C.: photocatalyst.