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. Author manuscript; available in PMC: 2022 Jun 16.
Published in final edited form as: J Am Chem Soc. 2021 Jun 4;143(23):8590–8596. doi: 10.1021/jacs.1c03563

Table 1.

Selected optimization experiments.a

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Entry Deviation from standard conditions Yield of 3a (%) (ax:eq)
1 - 84 (3.6:1)
2 L1 instead of dtbbpy 0
3 L2 instead of dtbbpy 10 (2.9:1)
4 L3 instead of dtbbpy <1
5 Without i-PrOH 63 (3.5:1)
6 1,4-Dioxane as solvent 40 (3.4:1)
7 Ni(cod)2 instead of NiBr2·DME 35 (3.8:1)
8 DIPEA instead of CS2CO3 0
9 Room temp instead of 80 °C <1
10 With air 0
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a

See Supporting Information (SI) for experimental details. Yields of 3a and axial:equatorial (ax:eq) ratios were determined by 1H-NMR using dibromomethane as the internal standard.