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. 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 3.

Comparison of Metal-Catalysts for Cycloaddition of Diynes and Nitrile.

graphic file with name nihms416666e3.jpg (3)
Entry [M] Catalyst x mol% equiv. of Nitrile a Temp Time Conva 1 Yielda,b 1a
1 5 mol% [Co]c 20 RT 24h 86% 70%
2 3 mol% [Rh]d 1.5 60 °C 3h >99% >99%
3 3 mol% [Rh]e 1.5 RT 3h 32% 15%
4 10 mol% [Ru]f 1.5 60 °C 24h 6%g -
5 3 mol% [Ni/SIPr]h 1.5 RT 3h >99% 80%
6 3 mol% [Ni/Xant]i 1.5 RT 3h >99% >99% (98%)
a

Analysed by GC using naphthalene as an internal standard.

b

Isolated yield in parenthesis.

c

5 mol% CoCl2, 6 mol% DPPE, xs Zn, diyne (1 equiv., 1 M), nitrile (20 equiv), NMP, RT.

d

3 mol% [Rh(COD)]BF4, 3 mol% Segphos, diyne (1equiv., 0.1 M), nitrile (1.5 equiv.), DCE, 60 °C.

e

Same conditions as in [d], but the reaction was run @ RT.

f

10 mol% Cp*Ru(COD)Cl, diyne (1 equiv., 0.1 M), nitrile (1.5 equiv.), DCE, 60 °C, 24 h.

g

Analysed by NMR.

h

3 mol% Ni(COD)2, 3 mol% SIPr, diyne (1 equiv., 0.1 M), nitrile (1.5 equiv.), THF, RT.

i

3 mol% Ni(COD)2, 3 mol% Xantphos, diyne (1 equiv., 0.1 M), nitrile (1.5 equiv.), toluene, RT.