Table 1. Screening of Conditions for the Pd-Catalyzed Arylation of 11a.
entry | solvent | Base (n equiv) | Conversion to 12af (isolated yield)a |
---|---|---|---|
1 | methanol | NaOAc (3.0) | >80b (50) |
2 | methanol | – | dec.c |
3 | acetonitrile | NaOAc (3.0) | quant. (79) |
4 | acetonitrile | – | dec.c |
5 | THF | NaOAc (3.0) | <30%b |
6 | THF | – | <10%d |
7 | DMAe | NaOAc (3.0) | <5b |
8 | DMAe | – | dec.c |
Conversion was determined by TLC and 1H NMR spectroscopy of the reaction solution.
Starting material 11 detected in 1H NMR spectrum.
dec: decomposition; no signals of 12af or 11a visible in 1H NMR spectrum.
Signals for 11a with MOM-ether cleavage observed in 1H NMR spectrum.
DMA: N,N-dimethylacetamide.