Table 1.

Optimization Studies

Entry[a]	Ar–X	Base	Solvent	Temp (°C)	Yield (%)
					2a	3a
1	PhI	KOtBu	PhMe	80	0	0
2	PhI	KOtBu	THF	60	0	0
3	PhI	KOtBu	MeCN	80	0	0
4[b]	PhI	KOtBu	DMF	80	58	17
5	PhI	KOtBu	DMSO	80	70	11
6[c]	PhI	KOtBu	DMSO	80	33	49
7[d]	PhI	KOtBu	DMSO	80	63	18
8[e]	PhI	KOtBu	DMSO	80	34	25
9[f]	PhI	KOtBu	DMSO	80	0	39
10	PhI	NaOtBu	DMSO	80	0	trace
11	PhI	KHMDS	DMSO	80	0	trace
12	PhI	LDA	DMSO	80	0	12
13	PhBr	KOtBu	DMSO	80	64	15
14	PhCl	KOtBu	DMSO	80	52	11
15	PhF	KOtBu	DMSO	80	0	10
16	PhOTf	KOtBu	DMSO	80	0	21

^[a]Conditions: 2 equiv indole, 1 equiv aryl halide, 4 equiv KOtBu [0.3] M, all solvents were rigorously degassed by freeze/pump/thaw.

^[b]time = 24 h,

^[c]Conditions: 1 equiv indole, 3 equiv aryl halide, 4 equiv KOtBu, [0.3] M.

^[d]Reaction in the absence of light.

^[e]solvent not degassed, N2 atmosphere,

^[f]solvent saturated with O₂, also O₂ atmosphere.