Chart 1. Ortho Borylation of Alkylbenzoatesa.

^a Reactions were run with 1.0 mmol substrate, 1.0 mmol B₂pin₂, 0.025 mmol 5, and 0.0125 mmol [Ir(OMe)(cod)]₂ in 1.0 mL THF. Yields are for isolated materials.

^b 2.0 mmol substrate was used.

^c 0.5 mol % [Ir(OMe)(cod)]₂ was used.

^d Reaction was run at 60 °C.

^e 2.0 mmol B₂pin₂, 0.025 mmol [Ir(OMe)(cod)]₂, and 0.050 mmol 5 were used.

^f 0.5 mmol substrate was used.

^g 1.25 mmol B₂pin₂ was used.

^h 5% diborylated material was isolated.

ⁱ 17% diborylated material was isolated.

^j 10% diborylated material was isolated.