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. Author manuscript; available in PMC: 2013 Jun 6.
Published in final edited form as: J Am Chem Soc. 2012 May 21;134(22):9102–9105. doi: 10.1021/ja303442q

Table 1.

Stereoconvergent Negishi Phenylation of a Racemic α-Bromonitrile: Effect of Reaction Parametersa

graphic file with name nihms379312u2.jpg
entry variation from the “standard” conditions ee (%) yield (%)b
1 none 94 98
2 no NiCl2 • glyme – <2
3 no L <2 3
4 PhZnX, instead of Ph2Zn 90 6
5 r.t., instead of −78 °C 4 16
6 1, instead of L 84 89
7 2, instead of L 8 88
8 3, instead of L 8 32
9 4, instead of L 32 25
10 0.6 equiv Ph2Zn 93 48
11 5% NiCl2 • glyme, 6.5% (S,S )-L 93 68
a

All data are the average of two experiments.

b

Yield determined by GC analysis versus a calibrated internal standard.