Table 1. Optimization of the Reaction Conditions^a.

entry	catalyst (10 mol %)	additive	x equiv	yield (%) of 3b
1	Pd(MeCN)4BF4		4	26
2	Pd(MeCN)2(OTf)2		4	27
3	Pd(MeCN)2(OTs)2		4	34
4	Pd(OAc)2		4	52
5	Pd(OAc)2	Ru(bpy)3Cl2·H2O	4	55
6	Pd(TFA)2		4	58
7	Pd(TFA)2	PTSA (2 equiv)	4	64
8	Pd(TFA)2	AgOAc (1 equiv)	4	50
9	Pd(TFA)2	Ag2CO3 (1 equiv)	4	30
10	Pd(TFA)2		2	38
11c	Pd(TFA)2		4	68
12d	Pd(TFA)2		4	15
13e	Pd(TFA)2		4	20
14	Pd/C		4	<5%
15f	Pd2dba3		4	<5%

^aAll reactions were carried out in 0.1 mmol scale.

^bYields refer to here are isolated yields.

^cTwo equiv of aryldiazonium salt added different of 30 min interval.

^dIsopropanol used as a solvent.

^eTHF used as a solvent.

^fHomocoupling product was isolated.