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- W2805939966 abstract "The development of a Pd(II)-catalysed enantioselective fluorination of C(sp3)-H bonds would offer a new approach to making chiral organofluorines. However, such a strategy is particularly challenging because of the difficulty in differentiating prochiral C(sp3)-H bonds through Pd(II)-insertion, as well as the sluggish reductive elimination involving Pd-F bonds. Here, we report the development of a Pd(II)-catalysed enantioselective C(sp3)-H fluorination using a chiral transient directing group strategy. In this work, a bulky, amino amide transient directing group was developed to control the stereochemistry of the C-H insertion step and selectively promote the C(sp3)-F reductive elimination pathway from the Pd(IV)-F intermediate. Stereochemical analysis revealed that while the desired C(sp3)-F formation proceeds via an inner-sphere pathway with retention of configuration, the undesired C(sp3)-O formation occurs through an SN2-type mechanism. Elucidation of the dual mechanism allows us to rationalize the profound ligand effect on controlling reductive elimination selectivity from high-valent Pd species." @default.
- W2805939966 created "2018-06-13" @default.
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- W2805939966 date "2018-06-11" @default.
- W2805939966 modified "2023-10-06" @default.
- W2805939966 title "Controlling Pd(iv) reductive elimination pathways enables Pd(ii)-catalysed enantioselective C(sp3)−H fluorination" @default.
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- W2805939966 doi "https://doi.org/10.1038/s41557-018-0048-1" @default.
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