Controlling Pd(IV) reductive elimination pathways enables Pd(II)-catalysed enantioselective C(sp3)-H fluorination was written by Park, Hojoon;Verma, Pritha;Hong, Kai;Yu, Jin-Quan. And the article was included in Nature Chemistry in 2018.Electric Literature of C8H4BrF3O This article mentions the following:
The development of a Pd(II)-catalyzed 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, authors report the development of a Pd(II)-catalyzed 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 stereochem. of the C-H insertion step and selectively promote the C(sp3)-F reductive elimination pathway from the Pd(IV)-F intermediate. Stereochem. anal. 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. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7Electric Literature of C8H4BrF3O).
2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Electric Literature of C8H4BrF3O
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary