Table 1.

Bis(trifluoromethylthiolation) of Silyl Aryl Triflates^a

entry	aryne precursor	product	yield (%)
1			75
2			76
3			84
4			78
5b			64
6b			71
7b			56
8			74 81c
9			69
10b			66
11			44
12			68
13b			65
14			41

^aReaction conditions: Aryne precursor (0.3 or 0.5 mmol), CsF (3 equiv), CF₃SSCF₃ (3.5 equiv), DME (2 mL), 24–48 h, 85 or 110 °C. Yields are isolated yields.

^bYield determined by NMR with PhCF₃ as an internal standard. DME is dimethoxyethane.

^cScale: 1.0 mmol. Please see Supporting Information for details.