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. Author manuscript; available in PMC: 2018 Aug 7.
Published in final edited form as: Org Lett. 2004 Aug 5;6(16):2661–2664. doi: 10.1021/ol049159x

Table 1.

ISES Evaluation of Bidentate Ligands for Ni(0)-Mediated Allylic Substitution.

graphic file with name nihms983015u2.jpg
a no. bidentate ligand bΔO.D.340/time (mAbs/min) c% conv
1 DPPB (6) 132 ± 16 71
2 (S,S)-SKEWPHOS (5b) 64 ± 12 39
3 (R)-BINAP (15a) 45 ± 10 28
4 (R,R)-Me-DUPHOS (10a) 30 ± 1 22
5 (S)-QUINAPd 18 f
6 (S,S)-Di-t-Bu-boxe 15 ± 2 f
a

Conditions for the biphasic ISES screen (YADH = yeast alcohol dehydrogenase and YAlDH = yeast aldehyde dehydrogenase) as described in the Supporting Information.

b

Obs’d rates (10 min) of NADH formation in units of ΔO.D.340 min−1. Unless otherwise indicated, ISES slopes are reported as mean ± SD (duplicate runs).

c

Reaction conditions: 200 mM 1, 10 mol% Ni(cod)2, 20 mol% ligand, LiHMDS (1 eq.), THF, rt, 15 min. Product:educt ratio estimated by NMR following work-up.

d

Ligand is (S)-1-(2-diphenylphosphino-1-naphthyl)isoquinoline.

e

Ligand is 2,2′-methylenebis[(4S)-4-t-butyl-2-oxazoline].

f

Trace product (crude NMR).