Fig. 3: Survey of the alkyl boranes. | Nature Communications

Fig. 3: Survey of the alkyl boranes.

From: Rapid and scalable photocatalytic C(sp2)–C(sp3) Suzuki−Miyaura cross-coupling of aryl bromides with alkyl boranes

Fig. 3

Conditions for Method A: 4CzIPN (5 mol %), NiCl2·glyme (10 mol %), dtbbpy (10 mol %), 2,6-lutidine (2 equiv.), 1 (1.0 equiv.) and 2 (0.5 mmol) in CH3CN (0.1 M). The solution was N2-bubbled and irradiated with a blue LED (λ = 456 nm) for 3 h. Conditions for Method B: 4CzIPN (5 mol %), NiCl2·glyme (10 mol %), dtbbpy (10 mol %), 4–dimethylaminopyridine (2 equiv.), 1 (2.0 equiv.) and 2 (0.5 mmol) in CH3OH (0.1 M). The solution was N2-bubbled and irradiated with a blue LED (λ = 456 nm) for 3 h. Alkyl boranes were generated on-demand from the corresponding alkenes via hydroboration with BH3 (for Method A) or 9-BBN (for Method B). Yields reported are after isolation. a with Method A: 74%, rr 10:1. See Section 2.3 in the Supplementary Information for additional details. rr: regioisomeric ratio. dr: diastereomeric ratio. Brsm: based on recovered starting material. 9-BBN: 9-borabicyclo[3.3.1]nonane.

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