Skip to main content
. Author manuscript; available in PMC: 2013 Jan 29.
Published in final edited form as: Angew Chem Int Ed Engl. 2011 Sep 20;50(45):10694–10698. doi: 10.1002/anie.201104475

Table 1.

Ligand Screening for Ni-Catalyzed Cycloaddition of a Diyne and a Nitrilea,b

graphic file with name nihms416666e2.jpg (2)
Entry Ligand (Ln) Catalyst loading Temp. 1a % Yieldc
1 PCy3 10 mol% 100 °C 27
2 PBu3 10 mol% 100 °C -
3 PPh3 10 mol% 100 °C 23
4 P(o-tol)3 10 mol% 100 °C 11
5 P(O-iPr)3 10 mol% 100 °C -
6 DPPE 10 mol% 100 °C -
7 DPPF 10 mol% 100 °C 21
8 rac-BINAP 10 mol% 100 °C 7
9 Xantphos 10 mol% 100 °C >99 (86)d
10 Xantphos 5 mol% 100 °C >99
11 Xantphos 3 mol% 100 °C >99
12 Xantphos 3 mol% RT >99 (98%)d,e
a

For Entries 1–5, 20 mol% Ln was used. For entries 6–9, 10 mol% Ln was used. For entry 10, 5 mol% Ln was used. For entries 11–12, 3 mol% Ln was used.

b

The reactions from entries 1–11 were analysed after 24h and >99% diyne conversion was observed for all the entries.

c

Analysed by GC using naphthalene as an internal standard.

d

Isolated yields in parentheses.

e

The reaction was completed in 3 h.