New CF2H-Synthon Enables Asymmetric Radical Difluoroalkylation for Synthesis of Chiral Difluoromethylated Amines DOI Creative Commons
Xi‐Sheng Wang, Peng Liu, Yan He

и другие.

Research Square (Research Square), Год журнала: 2024, Номер unknown

Опубликована: Окт. 29, 2024

Abstract The difluoromethyl group (CF₂H) is a crucial fluorinated moiety with distinctive biological properties, and the synthesis of chiral CF₂H-containing analogs has been recognized as powerful strategy in drug design screening. To date, most established method for accessing enantioenriched compounds involves enantioselective functionalization nucleophilic electrophilic CF₂H synthons. However, this approach limited by reaction scope, lower reactivity, reduced enantioselectivity. Leveraging unique fluorine effect, we designed synthesized novel radical synthon incorporating isoindolinone into alkyl halides asymmetric transformation. Here, report an efficient construction carbon stereocenters featuring via nickel-catalyzed Negishi cross-coupling. This demonstrates mild conditions, broad substrate excellent Given that optically pure difluoromethylated amines isoindolinones are key structural motifs bioactive compounds, offers practical solution drug-like molecules pharmaceutical research development.

Язык: Английский

Visible-Light-Induced Photoredox Construction of Trifluoromethylated Quaternary All-Carbon Centers and Tertiary Alcohols via C(sp3)–Si Bond Cleavage DOI
Dachang Bai,

Dandan Ma,

Lingna Chang

и другие.

Synthesis, Год журнала: 2024, Номер unknown

Опубликована: Окт. 10, 2024

Abstract The construction of trifluoromethylated quaternary carbon centers and tertiary alcohols is realized by organo-photoredox catalysis. process proceeds via visible-light-induced C(sp3)–Si bond cleavage for the generation α-trifluoromethylated benzyl radicals, which are readily trapped electron-deficient alkenes with excellent regioselectivity all-carbon centers. α-difluoromethyl counterparts also suitable this radical conjugate addition. Furthermore, in situ oxidation these radicals O2 from air affords high yields, extends Fleming–Tamao reaction to systems.

Язык: Английский

Процитировано

0
Enantioconvergent C(sp3)–C(sp) Cross-Electrophile Coupling Enabled by Halogen Atom Transfer DOI
Martin Oestreich, Hendrik F. T. Klare, Nektarios Kranidiotis‐Hisatomi

и другие.

Synfacts, Год журнала: 2024, Номер 20(07), С. 0715 - 0715

Опубликована: Июнь 14, 2024

Key words cross-electrophile coupling - halogen atom transfer nickel catalysis photoredox trifluoromethylated alkynes

Язык: Английский

Процитировано

0
New CF2H-Synthon Enables Asymmetric Radical Difluoroalkylation for Synthesis of Chiral Difluoromethylated Amines DOI Creative Commons
Xi‐Sheng Wang, Peng Liu, Yan He

и другие.

Research Square (Research Square), Год журнала: 2024, Номер unknown

Опубликована: Окт. 29, 2024

Abstract The difluoromethyl group (CF₂H) is a crucial fluorinated moiety with distinctive biological properties, and the synthesis of chiral CF₂H-containing analogs has been recognized as powerful strategy in drug design screening. To date, most established method for accessing enantioenriched compounds involves enantioselective functionalization nucleophilic electrophilic CF₂H synthons. However, this approach limited by reaction scope, lower reactivity, reduced enantioselectivity. Leveraging unique fluorine effect, we designed synthesized novel radical synthon incorporating isoindolinone into alkyl halides asymmetric transformation. Here, report an efficient construction carbon stereocenters featuring via nickel-catalyzed Negishi cross-coupling. This demonstrates mild conditions, broad substrate excellent Given that optically pure difluoromethylated amines isoindolinones are key structural motifs bioactive compounds, offers practical solution drug-like molecules pharmaceutical research development.

Язык: Английский

Процитировано

0