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. Author manuscript; available in PMC: 2017 Jan 18.
Published in final edited form as: Angew Chem Int Ed Engl. 2015 Dec 3;55(3):1070–1074. doi: 10.1002/anie.201507494

Table 1.

Optimization of Allylic Alkylation with Diphenylmethane 1a.[a]

graphic file with name nihms765615u2.jpg
Entry Ni Source Ni/DPPF (mol %) Solvent Yield[b] (%)
1 Ni(COD)2 5/10 DME 72
2 Ni(COD)2 5/5 DME 39
3 Ni(COD)2 5/7.5 DME 46
4 Ni(COD)2 5/10 THF 46
5 Ni(COD)2 5/10 CPME <5
6 Ni(COD)2 5/10 dioxane <5
7 Ni(COD)2 5/10 2-Me-THF 52
8 NiCl2 5/10 DME 35
9 NiBr2 5/10 DME 51
10 Ni(COD)2 7.5/15 DME 90 (88)[c]
[a]

Reactions conducted on a 0.1 mmol scale.

[b]

Yields determined by 1H NMR spectroscopy of the crude reaction mixtures.

[c]

Isolated yield after chromatographic purification.