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. Author manuscript; available in PMC: 2017 Nov 21.
Published in final edited form as: Angew Chem Int Ed Engl. 2016 Nov 4;55(48):15091–15095. doi: 10.1002/anie.201609489

Table 1.

Selected optimization conditions with allene 1a

graphic file with name nihms835909u2.jpg
Entry Ni (mol%) Ligand (mol%) Temp (°C) Solvent Conv.(%) Yield (%)[a]
1 10% dppp (12) 100 Tol 100 0
2 10% dppb (12) 100 Tol 100 0
3 10% dppe (12) 100 Tol 100 0
4 10% BINAP (12) 100 Tol 100 0
5 10% PPh3 (24) 100 Tol 100 92
6 10% PCy3 (24) 100 Tol 100 80
7 10% PPh3 (12) 100 Tol 100 92
8 10% PPh3 (12) 100 THF 100 85
9 10% PPh3 (12) 100 1,4-dioxane 100 86
10 5% PPh3 (6) 100 Tol 100 91
11 2.5% PPh3 (3) 100 Tol 75 71
12[b] 10% PPh3 (12) 25 Tol 100 91
[a]

Determined by 1H NMR using mesitylene as the internal standard. PCy3 = tricyclohexylphosphine. cod = 1,5-cyclooctadiene.

[b]

72 h.