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. 2018 Oct 22;9:4393. doi: 10.1038/s41467-018-06830-w

Table 1.

Optimization of the defluorosilylation process

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Entry Conditions 3a (%)a Entry Conditions 3a (%)a
1 Ni(COD)2, KOtBu, PhMe, 110 °C, 24 h 56 7 Ni(COD)2, KOMe, c-hexane/THF 1/2 60
2 Ni(COD)2, KOtBu, other solvents (e.g., c-hexane) ≤74 8 Ni(COD)2, KHMDS, c-hexane/THF 1/2 56
3 Ni(COD)2, KOtBu, c-hexane/THF 4/1 74 9 Ni(PPh3)2Cl2, KOtBu, c-hexane/THF 1/2 20
4b Ni(COD)2, KOtBu, c-hexane/THF 1/2 89 10 Ni(acac)2, KOtBu, c-hexane/THF 1/2 12
5 Ni(COD)2, KOtBu, c-hexane/THF 1/4 59 11b none metal catalyst, KOtBu, c-hexane/THF 1/2 0
6 Ni(COD)2, NaOtBu, c-hexane/THF 1/2 71 12b Ni(COD)2, none base, c-hexane/THF 1/2 0

Reaction conducted on 0.2 mmol scale, 80 °C, 24 h

aYield by gas chromatography. The reaction conditions (entry 4) are optimal

brt, 2 h