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. 2024 Dec 7;89(24):18585–18601. doi: 10.1021/acs.joc.4c02520

Table 1. Screening of Conditions for the Pd-Catalyzed Arylation of 11a.

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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
a

Conversion was determined by TLC and 1H NMR spectroscopy of the reaction solution.

b

Starting material 11 detected in 1H NMR spectrum.

c

dec: decomposition; no signals of 12af or 11a visible in 1H NMR spectrum.

d

Signals for 11a with MOM-ether cleavage observed in 1H NMR spectrum.

e

DMA: N,N-dimethylacetamide.