Table 1. Optimization of the Direct Arylation of Complex 1a and 4-Iodotoluene (2a)^a.

entry	R–CO2H	additive (2 equiv)	T (°C)	3aa:3aa′:3aa″ yield (%)b
1	1-AdCO2H	–	60	58:3:1
2	PhCO2H	–	60	34:1:1
3	p-NO2–C6H4–CO2H	–	60	0:0:0
4	p-NMe2–C6H4–CO2H	–	60	52:3:5
5	1-AdCO2H	piperidine	60	0:0:0
6	1-AdCO2H	Et3N	60	57:3:3
7	1-AdCO2H	TMP	60	78:3:5
8	1-AdCO2H	TMP	50	69:3:5
9c	1-AdCO2H	TMP	60	52:5:6
10	–	TMP	60	39:2:1
11d	1-AdCO2H	TMP	60	0:0:0
12e	1-AdCO2H	TMP	60	0:0:0

^aReactions carried out on 0.1 mmol scale with respect to 2a.

^bYield determined by ¹H NMR of the crude using an internal standard.

^cNo K₂CO₃ was added.

^dNo Ag₂CO₃ was added.

^e20 equiv of (ethoxymethoxy)benzene were used instead of complex 1a.