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. 2019 May 22;10(24):6210–6214. doi: 10.1039/c9sc02067e

Scheme 5. Formal alkene hydromethylation. Homologation: 14a–k (0.05–0.2 mmol, 1.0 equiv.), CH2Br2 (2.0–3.0 equiv.), n-butyllithium (1.5–2.0 equiv.) in THF or Et2O: protodeboronation: 15a–k (0.05–0.2 mmol, 1.0 equiv., used as crude from homologation step), PhLi (1.1 equiv.), Et2O (0.5–2.0 mL), thiophenol (1.1 equiv.), PC1 (2.5 mol%) in MeOH/acetone (1 : 1, 0.5–2.0 mL). Yield corresponds to the two-step homologation-protodeboronation sequence. For the hydroboration step, we refer to the ESI. aDerived from O-Ts-protected phenol, O–S cleavage during reaction.

Scheme 5