Table 1.

Optimization of reaction conditions^[a][b]

Entry	Variation from “standard conditions”	conv. (3a)	4a	2d
1	none	100%	95% (93%)	<5%
2	AgSbF6	100%	73%	25%
3	60 °C	100%	65%	30%
4	rt	20%	15%	<5%
5	DCB as solvent	100%	89%	10%
6	MeOH as solvent	50%	45%	<5%
7	Add 1 eq. K3PO4	100%	87%	10%
8	Add 1 eq. KOAc	<5%	0%	0%
9	Mor-DalphosAuCl 5 mol%	20%	15%	<5%
10	No [Au]	0%	-	-
11	No [Ag]	0%	-	-
12	No ArI	No conversion on 1a
13	dppm(AuBr)2 10 mol%, ArB(OH)2, Selectfluor, MeCN/MeOH, 50 °C		20%
14	PPh3AuCl 10 mol%, ArN2BF4, [Ir] cat. MeOH, rt, hv		0%

^[a]Conditions: 1a (0.4 mmol), MeOH (0.6 mmol), 3a (0.2 mmol), Au cat. (0.01 mmol), AgOTf (0.21 mmol), DCM (2 mL), 40 °C, 12 h.

^[b]1H NMR yields using 1,3,5-tribromobenzene as an internal standard (isolated yields).