Table 1.

Photoinduced, copper-catalyzed coupling of an aliphatic amine with an unactivated secondary alkyl iodide: Effect of reaction parameters.

entry	variation from the “standard” conditions	yield (%)a
1	none	92
2	no Cul	<1
3	no rac-BINOL	<1
4	no hv	<1
5	no BTPP	<1
6	no Cul, no rac-BINOL, no light	<1
7	CuBr, instead of Cul	84
8	CuCI, instead of Cul	86
9	CuBr2, instead of Cul	81
10	Cu(OTf)2, instead of Cul	82
11	copper nanopowder, instead of Cul	<1
12	6% rac-BINOL	70
13	4% rac-BINOL	48
14	2-naphthol, instead of rac-BINOL	14
15	rac-BINOL dimethyl ether, instead of rac-BINOL	<1
16	1,1,3,3-tetramethylguanidine, instead of BTPP	50
17	LiOt-Bu, instead of BTPP	14
18	room temperature	56
19	1.2 equiv Cyl	62
20	1.0 equiv BTPP	62
21	2.5% Cul, 5% rac-BINOL	54
22	CyBr, instead of Cyl	<1
23	CyCI, instead of Cyl	<1
24	CyOTs, instead of Cyl	<1
25	under air (capped vial)	39
26	0.1 equiv H2O added	78

^aYields were determined via ¹H NMR analysis versus an internal standard (average of two experiments).