Table 4. Optimization and Controls^a.

entry	notes	X	Y	22	20	21
1		0.35	2.50	69	5	4
2		0.35	2.25	72 (60)	6	6
3		0.35	2.0	56	7	8
4		0.35	1.5	50	9	15
5b		0.40	2.0	51	7	8
6c		0.45	2.0	42	3	5
7c		0.50	2.0	32	3	4
8d	no NaI	0.35	2.0	0	0	0
9	LiI for NaI	0.35	2.0	49	7	7
10	KI for NaI	0.35	2.0	48	4	8
11	5 mol % catalyst	0.35	2.0	42	6	9
12e	no dtbbpy	0.35	2.25	0	0	2
13e,f	no Ni or Zn	0.35	2.0	0	0	1
14e,g	no Ni	0.35	2.0	<1	<1	0
15c,g	no Zn	0.35	2.25	25	<1	4
16	6/1 DMA/THF	0.35	2.25	76	7	0
17	1/1 DMA/THF	0.35	2.25	52	7	3
18e,g	1/2 DMA/THF	0.35	2.25	<1	0	1

^aReactions were run on a 0.75 mmol scale in 3 mL of DMA. Yields are uncorrected GC yields vs dodecane. The yield in parentheses is an isolated yield of purified product.

^bPhBr (8%) remained.

^cPhBr (27%–47%) remained.

^dStarting materials were unchanged after 40 h, except for a 13% yield of hydrodehalogenated 19.

^ePhBr (75%) remained.

^fAlkyl-Br 19 not consumed.

^gDialkyl ketone (12–23%) was formed.