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. 2018 Dec 4;10(6):1780–1785. doi: 10.1039/c8sc04279a

Table 1. Variation of the reaction parameters for the Ni-catalysed reductive arylalkylation reaction a .

Inline graphic
Entry Variation from the optimum conditions Yield 3a b (%) Yield: 3a-1 b (%)
1 None 69 (67 c ) 9
2 Iodo-analogue of 1a used 32 19 (8 d )
3 Iodo-analogue of 2a used 10 18 (31 d )
4 Both iodo-analogues of 1a and 2a used 17 10 (30 d )
5 L2 instead of L1 30 49
6 L3 instead of L1 45 2
7 L4 instead of L1 54 13
8 L5 instead of L1 32 50
9 L6 instead of L1 0 0
10 NiI2 instead of NiBr2 61 8
11 Ni(OTf)2 instead of NiBr2 32 4
12 NiBr2·glyme instead of NiBr2 63 8
13 Ni(COD)2 instead of NiBr2 63 7
14 DMF instead of DMA 43 3
15 NMP 68 8
16 THF instead of DMA 0 0
17 MeCN instead of DMA 0 0
18 Mn instead of Zn 51 17
19 75 °C instead of 55 °C 62 8
20 35 °C instead of 55 °C 27 2
21 1.2 equiv. 2a used 50 13
22 10 mol% NiBr2 used 63 13
23 2 equiv. Zn used 50 7

aUnless otherwise specified, reactions were performed on a 0.2 mmol scale of aryl bromide 1a with 2 equiv. bromobutyl acetate (2a), 15 mol% NiBr2, 15 mol% ligand L1 and 4 equiv. Zn as the reductant in 0.5 mL DMA at 55 °C for 10 h.

bGC-yields using n-dodecane as an internal standard.

cYield of the isolated product.

dYield of 3a-2.