Fig. 2.

Optimization of regiodivergent remote hydrothiolation. *Yields were determined by gas chromatography (GC) analysis using n-tetradecane as the internal standard. The yield within parentheses is the isolated yield and is an average of two runs (0.20 mmol scale). ^†r.r. refers to regioisomeric ratio, representing the ratio of the major product to the sum of all other isomers as determined by GC analysis. ^‡The linear thioether (3A) is obtained as a single isomer; conditions B for terminal selectivity: NiI₂ (5 mol%), L2 (6 mol%), (MeO)₂MeSiH (3.5 equiv.), DMSO (0.50 M), 50 °C, 48 h. Ph, phenyl; Bn, benzyl; ⁿPr, n-propyl; HBpin, pinacolborane; THF, tetrahydrofuran; DMSO, dimethyl sulfoxide