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. Author manuscript; available in PMC: 2013 Aug 17.
Published in final edited form as: Org Lett. 2012 Jul 31;14(16):4182–4185. doi: 10.1021/ol301847m

Table 1.

Optimization of amination using Ni(II) precatalysta

graphic file with name nihms398141u2.jpg
entry substrate Ni source reducing agent yieldb
1 1 Ni(acac)2 Zn dustc 0%
2 1 NiCl2(DME) Zn dustc 0%
3 1 Ni(acac)2 H–SiEt3c 0%
4 1 NiCl2(DME) H–SiEt3c 51%
5 1 Ni(acac)2 Ph–B(OH)2 57%
6 1 NiCl2(DME) Ph–B(OH)2 98%
7 2 NiCl2(DME) Ph–B(OH)2 variable
8 2 NiCl2(DME) (Ph–BO)3 58%
9 2 NiCl2(DME) Ph–B(pin) 94%
10 1 NiCl2(DME) Ph–B(pin) 92%
a

Conditions: Ni(II) complex (5 mol %), 3 (10 mol %), sulfamate/carbamate substrate (1 equiv), piperidine (1.2 equiv), reducing agent (0.55 equiv), NaOtBu (1.85 equiv), hexamethylbenzene (0.1 equiv), 3 h.

b

Yield determined by 1H NMR analysis of the crude reaction mixtures using hexamethylbenzene as an internal standard.

c

Reducing agent (0.8 equiv) and NaOtBu (1.4 equiv).