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. Author manuscript; available in PMC: 2022 Aug 6.
Published in final edited form as: Org Lett. 2021 Jul 23;23(15):5703–5708. doi: 10.1021/acs.orglett.1c01790

Table 1.

Variations of reaction conditions.a

graphic file with name nihms-1748418-t0002.jpg
entry Deviation from standard conditions E*ox
vs SCE		 yield e.e.
1 None + 1.21 V 82% 95%
2 [Ru(bpy)3]Cl2 instead of Ir, rt + 0.77 V 0% -
3 [Ru(bpz)3]Cl2 instead of Ir, rt + 1.45 V 0% -
4 MesAcrMe+ instead of Ir, rt + 2.06 V 45% 83%
5 TPPT instead of Ir, rt + 2.30 V 16% 85%
6 rt instead of −25 °C + 1.21 V 71% 87%
7 no light + 1.21 V 0% -
8 no photocatalyst - 0% -
9 no Sc(OTf)3 + 1.21 V 0% -
10 no Bu4NCl + 1.21 V 72% 90%
11 ScCl3 instead of Sc(OTf)3 + 1.21 V 0% -
a

Reaction conditions: 1a (0.15 mmol, 1 equiv), 2a (0.225 mmol, 1.5 equiv), photocatalyst (3 × 10–3 mmol, 2 mol%), Sc(OTf)3 and Bu4NCl (0.0225 mmol, 15 mol%), (S,S)-sBuPybox (0.03 mmol, 20 mol%), MeCN (3.0 mL, 0.05 M), 34 W blue LEDs. Yields determined by 1H NMR analysis of crude reaction mixtures using mesitylene as internal standard.