Beilstein J. Org. Chem.2020,16, 1627–1635, doi:10.3762/bjoc.16.135
Selectfluor® and amine/HF mixtures, the formation of protected α-fluoroketones from simple alkynes was realised. Whilst the transient p-TolIF2 species generated in situ productively engaged with pentynyl benzoate scaffolds to generate the desired α-fluoroketone motif, augmentation or contraction of the linker
suppressed catalysis. The prerequisite for this substructure was established by molecular editing and was complemented with a physical organic investigation of possible determinants.
Keywords: α-fluoroketone; alkyne; fluorination; hypervalent iodine; organocatalysis; Introduction
The venerable role of
, entry 1), whereas increasing the Brønsted acidity to 1:7.5 furnished the desired α-fluoroketone 2 in 64% yield (Table 1, entry 2). However, employing Olah’s reagent (1:9.23) had a negative impact on the efficiency (45% yield, Table 1, entry 3) thereby allowing a plateau to be established (vide infra
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Graphical Abstract
Figure 1:
(A) Synthetic routes to α-fluoroketones from silyl enol ethers or acetophenone derivatives. (B) Sel...