Table 1. Initial Screening of the Reaction Conditions for the Benchmark Reaction.

entrya	ligand	base	time	Pd/ligand ratiob	homocouplingd	yield
1	SPhos	Na2CO3	14 h	1:2.5	5%	36%
2	SPhos	K2CO3	14 h	1:2.5	2%	60%
3	SPhos	Cs2CO3	14 h	1:2.5	3%	39%
4	XPhos	Na2CO3	14 h	1:2.5	2%	44%
5	XPhos	K2CO3	14 h	1:2.5		35%
6	XPhos	Cs2CO3	14 h	1:2.5	1%	44%
7c	XPhos	K2CO3	60 h	1:2.5		85%
8c	SPhos	K2CO3	60 h	1:2.5	2%	90%
9	XPhos	K2CO3	60 h	1:1.5		99%
10	SPhos	K2CO3	60 h	1:1.5		89%

^aReactions (except entry 10 and 11) were performed on a 0.18 mmol scale with 1 equiv of 1 and 2 and 2.2 equiv of the base at 95 °C.

^bAs Pd source 5% Pd₂(dba)₃ was used resulting in 10% catalyst load.

^cThese reactions were performed on a 1.8 mmol scale with 1 equiv of 1 and 2 and 2.2 equiv of the base and 3% Pd₂(dba)₃.

^dHomocoupling was determined by GC or ¹⁹F-NMR.