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. Author manuscript; available in PMC: 2023 Dec 28.
Published in final edited form as: J Am Chem Soc. 2022 Dec 15;144(51):23685–23690. doi: 10.1021/jacs.2c11501

Table 1.

Exploration of the reaction conditionsa for the photochemical synthesis of functionalized bicyclo[3.1.1]heptanes.

graphic file with name nihms-1922169-t0002.jpg
Entry Solvent PC Yield of 3 (%)b
1 DMSO Ir[dF(CF3)ppy]2(dtbpy)PF6 72 (70)e
2 DMSO Ir(ppy)3 <10
3 DMSO Ru(bpy)3(PF6)2 30
4 DMSO MesAcr traces
5 DMSO 4CzIPN 27
6 DMA Ir[dF(CF3)ppy]2(dtbpy)PF6 46
7 MeCN Ir[dF(CF3)ppy]2(dtbpy)PF6 40
8 1,4-dioxane Ir[dF(CF3)ppy]2(dtbpy)PF6 0
9 MeNO2 Ir[dF(CF3)ppy]2(dtbpy)PF6 traces
10 DMSO none 0
11c DMSO Ir[dF(CF3)ppy]2(dtbpy)PF6 0
12d DMSO Ir[dF(CF3)ppy]2(dtbpy)PF6 0
a

Reaction conditions: 1a (0.1 mmol, 1 equiv), 2a (0.2 mmol, 2 equiv), photocatalyst (2 mol % metal-based PC or 5 mol % organic based PC), in dry and degassed solvent (0.2 M) under blue Kessil irradiation (λmax = 427 nm) at rt.

b

Yields determined by 1H NMR using 1,3,5-trimethoxybenzene as internal standard.

c

Reaction in the absence of light irradiation.

d

Reaction as in entry 5 but in the presence of 5 equiv of TEMPO.

e

Isolated yield from 0.2 mmol scale.