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. Author manuscript; available in PMC: 2009 Aug 3.
Published in final edited form as: J Am Chem Soc. 2006 Mar 1;128(8):2609–2614. doi: 10.1021/ja057741q

Table 1.

Reaction Optimizationa

graphic file with name nihms-82846-t0003.jpg
entry ligand solvent temp (°C) time (min) % yield (dr)
1 dppe THF 60 30 42
2 PCy3 THF 60 30 20
3 P(t-Bu)3 THF 25 10 35
4 none THF 0 10 64 (4.8:1)
5 none dioxane 90 30 54 (3.5:1)
6 none toluene 60 5 45 (>19:1)
7 none THF 25 5 72 (5.3:1)
8 none THF 60 5 68 (>19:1)
a

Entries 1-4: 1a (1.0 equiv) was added to a premixed solution of TMSCHN2 (2.0 equiv) and Ni(COD)2 (10 mol %). Entries 5-8: Ni(COD)2 (10 mol %) was added to a premixed solution of 1a (1.0 equiv) and TMSCHN2 (2.0 equiv).