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. Author manuscript; available in PMC: 2019 Sep 12.
Published in final edited form as: J Am Chem Soc. 2018 Jul 26;140(36):11317–11324. doi: 10.1021/jacs.8b05868

Table 3.

Formation of Quaternary Center Optimization

graphic file with name nihms-987197-t0009.jpg

Entry Deviation from “Standard Conditions” Yield (%)a
1 10 mol% NiBr2(dtbbpy) none graphic file with name nihms-987197-t0010.jpg
2 No NMP none
3 No MnO2 20
4 Under O2 instead of air tracec
5 1 equiv H2O none
6 5 mol% NiBr2(diglyme) 54
7 2 equiv Mn 43
8 1 equiv Ph(i-PrO)SiH2 28
9 No NiBr2(diglyme) none
10 No Fe(dpm)3 none
a

0.1 mmol scale, yield determined by FID using dodecane as an internal standard.

b

0.3 mmol scale, isolated yield.

c

Under an O2 balloon, the olefin was predominantly consumed to hydration via Drago—Mukaiyama Hydration.