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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 2.

Scope of cross-coupling reaction of alkylmagnesium bromides.graphic file with name nihms-563658-t0002.jpg

Entry Product Yield [%][a] S.M. ee [%][b] Prod ee [%][b] es [%]
1 graphic file with name nihms-563658-t0003.jpg 5 80 92 91 99
2 6 R2 = nPr 93 97 97 >99
3 7 R2 = nPent 91 97 97 >99
4 graphic file with name nihms-563658-t0004.jpg 8 R2 = (CH2)3Ph 88 97 97 >99
5 [c] 9 R2 = graphic file with name nihms-563658-t0005.jpg 81 97 97 >99
6[d] 10 R2 = (CH2)3CF3 68 >99 97 97
7 11 R2 = iBu 40 97 90 93
8 graphic file with name nihms-563658-t0006.jpg 12 R2 = nPr 80 93 92 99
9 13 R2 = (CH2)3Ph 88 93 93 >99
10[c] graphic file with name nihms-563658-t0007.jpg 14 93 97 97 >99
11[e] graphic file with name nihms-563658-t0008.jpg 15 54 99 96 97
12[f] graphic file with name nihms-563658-t0009.jpg 16 67 >99 91 91
[a]

Calculated yield after silica gel chromatography.

[b]

Determined by chiral SFC chromatography, S.M. = starting material, Prod. = product.

[c]

5 mol % Ni(dppe)CI2.

[d]

10 mol % Ni(dppe)CI2.

[e]

Ni(dppe)CI2 was added in two aliquots of 5 mol %; see SI for details.

[f]

5 °C; 48 h; 15% 2-benzylnapthalene byproduct.