Recent Advance in the C−F Bond Functionalization of Trifluoromethyl Aromatic and Carbonyl Compounds

ChemCatChem, Год журнала: 2023, Номер 16(8)

Опубликована: Дек. 28, 2023

Abstract The selective C−F bonds functionalization in available trifluoromethyl compounds is an economic route for obtaining high‐value organic fluorine compounds. However, due to the high dissociation energy group, strength of bond decreases continuously during defluorination, posing a challenge modifying such molecules without over‐conversion. Over past few years, there has been significant progress developing efficient methods constructing difluoromethylene unit, using approaches as radical chemistry, photochemistry, electrochemistry, and organometallic chemistry. These involve difluorocarbon radicals, cations, anions, carbenes intermediates. In this review, we summarized recent five years research achievements field single cleavage aromatic carbonyl gain diverse difluoromethylene‐containing via different intermediate strategies.

Язык: Английский

---

Visible Light-Induced 1,2-Diphenyldisulfane-Mediated Defluoroborylation of Polyfluoroarenes

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(7), С. 5049 - 5059

Опубликована: Март 16, 2024

A green and practical protocol of defluoroborylation polyfluoroarenes with stable readily accessible NHC-borane was developed, using 1,2-diphenyldisulfane as a hydrogen atom transfer (HAT) single electron (SET) reagent precursor under visible-light irradiation, leading to the concise formation value-added fluorinated organoboron scaffolds. Mechanism studies revealed method underwent boryl radical addition reaction polyfluoroarene, followed by successive pathways defluorination C–F bond offer targeted product. This unprecedented platform relies on base without expensive photocatalysts, highlighting methodology has promising application value prepare borylated polyfluoroarene compounds.

Язык: Английский

---

Defluorinative Multicomponent Cascade Reaction of Trifluoromethylarenes via Palladium Photoredox Catalysis

Опубликована: Май 20, 2024

The incorporation of aromatic difluoromethyl motifs has proven to be a fruitful strategy for enhancing the therapeutic profiles modern pharmaceutical candidates. While defluorofunctionalization trifluoromethylarenes offers promising pathway towards diverse compounds, current methods are predominantly limited two-component reactions. Multicomponent cascade reactions (MCRs) involving transient radical still uncommon and highly sought after owing their capacity rapidly generate challenging molecular structures. In this study, we present photocatalytic manifold that combines commercially available trifluoromethylarenes, feedstock dienes various nucleophiles achieve modular defluorinative MCR. This method features mild reaction conditions broad substrate scope with excellent functional group compatibility. Furthermore, protocol enables previously unreported process formal editing resulting MCR adducts. Preliminary mechanistic studies support proposed photoinduced palladium catalytic cycle.

Язык: Английский

---

One-pot C(sp³)-H difluoroalkylation of tetrahydroisoquinolines and isochromans via electrochemical oxidation and organozinc alkylation

Chemical Communications, Год журнала: 2024, Номер 60(50), С. 6395 - 6398

Опубликована: Янв. 1, 2024

The C(sp

Язык: Английский

---

Cross-coupling of trifluoromethylarenes with alkynes C(sp)-H bonds and azoles C(sp2)-H bonds via photoredox/copper dual catalysis

Chinese Chemical Letters, Год журнала: 2024, Номер unknown, С. 110505 - 110505

Опубликована: Сен. 1, 2024

Язык: Английский

---