Skip to main content
. Author manuscript; available in PMC: 2018 Apr 12.
Published in final edited form as: J Am Chem Soc. 2018 Feb 21;140(9):3394–3402. doi: 10.1021/jacs.7b13616

Table 1.

Optimization of asymmetric PCET reaction.a

graphic file with name nihms956192u2.jpg
Entry graphic file with name nihms956192t1.jpg photocatalyst base (loading) additive (equiv) % yield % ee
1 Me [Ru(bpy)3](BArF)2 TRIP (20 mol%) — 17 25
2 CO2Me [Ru(bpy)3](BArF)2 TRIP (20 mol%) — 21 52
3 Cbz [Ru(bpy)3](BArF)2 TRIP (20 mol%) — 14 86
4 Cbz [Ru(bpy)3](BArF)2 TRIP (20 mol%) TEMPO-H (0.2 equiv) 0 —
5 Cbz Ir(ppy)3 TRIP (5 mol%) PhI(OAc)2 (1.0 equiv) 71 58
6 Cbz Ir(ppy)3 TRIP (5 mol%) TIPS-EBX (1.0 equiv) 73 89
7 Cbz Ir(ppy)3 H8-TRIP (3 mol%) TIPS-EBX (1.5 equiv) 91 93
graphic file with name nihms956192t2.jpg
a

Optimization studies were performed on 0.05 mmol scale. Yields were determined by 1H-NMR analysis of the crude reaction mixtures relative to an internal standard. Enantiomeric excess was determined by HPLC analysis on a chiral stationary phase.