Table 1.

Coupling of aryl halides with TIPS-SH catalyzed by Pd(OAc)₂ and CyPF-tBu ligand.^[a]

Entry	ArX	Cat. [mol%]	Product	Yield [%]
1		0.05		98
2[b]		0.05		88
3[c]		0.05		90
4[d]		0.1		91
5[e]		0.1		96
6		0.05		91
7		0.25		96
8		0.25		99
9		0.25		76
10		0.25		87
11		0.25		74
12		0.05		97
13		0.05		95[f]

^[a]Reactions were conducted with a 1:1 ratio of metal to ligand, 1 mmol of both ArX and thiol, and 1.1 equiv of LiHMDS at 110°C in toluene (1.5 mL) requiring 2–4 h to complete.

^[b]Reaction performed with NaOtBu as base.

^[c]Reaction conducted in DME.

^[d]Reaction performed at 90°C.

^[e]Reaction required 12 h to complete.

^[f]TBAF (2 equiv) was added to the crude mixture and stirred 30 min at RT.