Table 1.

Effect of reaction parameters on the enantioconvergent deoxygenative reductive cross-coupling reaction

entry	variation from the “standard conditions”	yield (%)a	ee (%)b
1	None	83	92
2	No Ni, PC, Quinuclidine, or light	0	‒
3	No (S)-L1	13	0
4	No 4-Methylpyridine	23	25
5	L2, instead of (S)-L1	18	60
6	L3, instead of (S)-L1	12	‒34
7	L4, instead of (S)-L1	15	25
8	L5, instead of (S)-L1	0	‒
9	L6, instead of (S)-L1	30	31
10	Pure MTBE	62	82
11	Pure i-PrOH	2	87
12	NaOAc, instead of Quinuclidine	13	84
13	Pyridine, instead of 4-Methylpyridine	70	88
14	2.5 mol% NiBr2•DME, 3.0 mol% (S)-L1	39	92
15	9 h, instead of 18 h	67	92
16	r.t., instead of 10 oC	23	88
17	1.0 mL air added (4 mL reaction vial)	70	89
18	0.1 equiv H2O added	32	80
19	S1, S2, or S3, instead of β-hydroxy ketone	<1	–

MTBE methyl tert-butyl ether, DME 1,2-dimethoxyethane, PC (Ir[dF(CF₃)ppy]₂(dtbpy))PF₆, LED light emitting diode. The green circle signifies an enantioenriched compound.

^aDetermined through GC analysis.

^bDetermined through HPLC analysis.