Table 4.

Insertion of Arynes into Si–S Bonds^a

^aArX (1 equiv), Me₃SiSEt (3 equiv), base (2 equiv), diethyl ether/C₆H₁₂ (1:1, 3 mL) for ArOTf, diethyl ether (3 mL) for ArHal, 0.5 mmol scale, yields are isolated yields. See the Supporting Information for details.

^bProduct contains 4% of an isomeric impurity.

^cCrude mixture contains another isomer (4.2:1), which was separated during chromatography.

^dYields are of pure isomers, separated by column chromatography.

^eReaction mixture contained another isomer (16:1), which was separated by column chromatography.

^fYields are of pure isomers, separated by column chromatography. Crude isomer ratio 1.9:1.