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. Author manuscript; available in PMC: 2014 Apr 18.
Published in final edited form as: Angew Chem Int Ed Engl. 2014 Jan 29;53(9):2422–2427. doi: 10.1002/anie.201308666

Table 3.

Scope of cross-coupling reaction of arylmagnesium bromides.graphic file with name nihms-563658-t0010.jpg

Entry Product Ni(dppe)CI2 [mol %] Yield [%][a] S.M. ee [%][b] Prod ee [%][b] es [%]
1 graphic file with name nihms-563658-t0011.jpg 17 R = H 2 67 >99 91 92
2 18 R = NMe2 5 80 >99 nd[c] nd[c]
3 19 R = OMe 2 86[d] >99 97 97
4 20 R = F 2 82[d] >99 87 88
5 graphic file with name nihms-563658-t0012.jpg 21 10 76 >99 93 94
6 graphic file with name nihms-563658-t0013.jpg 22 5 80 >99 85 86
7 graphic file with name nihms-563658-t0014.jpg 23 4 92[d] 96 88 92
8 graphic file with name nihms-563658-t0015.jpg 24 10 71 97 95 98
9[e] graphic file with name nihms-563658-t0016.jpg 25 20 76 99 93 94
[a]

Isolated yield after silica gel chromatography.

[b]

Determined by chiral SFC.

[c]

nd = not determined; enantiomers are inseparable by chiral SFC chromatography.

[d]

Calculated yield; see SI for details.

[e]

Ni(dppe)CI2 was added in two aliquots of 10 mol %; see SI for details.