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. Author manuscript; available in PMC: 2011 Aug 18.
Published in final edited form as: J Am Chem Soc. 2010 Aug 18;132(32):10961–10963. doi: 10.1021/ja104896b

Table 2.

α-Selective Ni-Catalyzed Hydroalumination of Arylacetylenesa

graphic file with name nihms222574t2.jpg
entry aryl temp (°C) time (h)b conv (%)c α:βc
1 o-OMeC6H4 4 12 >98 98:2
2 m-OMeC6H4 22 2 >98 >98:2
3 p-OMeC6H4 4 12 >98 >98:2
4 m-CF3C6H4 4 12 >98 95:5
5 p-CF3C6H4 22 2 >98 97:3
6 p-FC6H4 22 2 >98 >98:2
7 o-ClC6H4 22 2 >98 >98:2
8 o-BrC6H4 22 2 >98 >98:2
9 o-MeC6H4 4 12 >98 >98:2
10 3-pyridyl 22 2 >98 >98:2
11 3-pyridyl 22 2 >98 >98:2
a

Reactions under N2 atm.

b

Reaction times correspond to hydroalumination portion of the process (not including D2O quench).

c

By analysis of 400 MHz 1H NMR spectra of unpurified mixtures (after D2O); <2% alkynylaluminum observed.