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. 2021 Apr 22;86(9):6259–6277. doi: 10.1021/acs.joc.1c00042

Table 1. Reaction Conditions for the C–H Olefination of (±)-16.

graphic file with name jo1c00042_0014.jpg

entry temp. (°C) x time (h) 1H NMR yielda
1 80 1.5 16 49%
2 60 1.5 16 31%
3 80 1.5 6 45%
4 80 1.0 16 42%
5 80 2.0 16 54% (59%b,c+ 5%b,d)
6e 80 1.5 16 55%
a

1H NMR yield of the desired regioisomer was determined by using CH2Br2 as the internal standard.

b

Isolated yield.

c

Regioselectivity was determined from the crude mixture: A/B = 6:1.

d

Diolefinated product.

e

15 mol % of Pd(OAc)2 and S,O-ligand were used.