Journal ArticleDOI
Radical Addition Enables 1,2-Aryl Migration from a Vinyl-Substituted All-Carbon Quaternary Center
Reads0
Chats0
TLDR
An efficient method for photocatalytic perfluoroalkylation of vinyl-substituted all-carbon quaternary centers involving 1,2-aryl migration has been developed in this article.Abstract:
An efficient method for photocatalytic perfluoroalkylation of vinyl-substituted all-carbon quaternary centers involving 1,2-aryl migration has been developed. The rearrangement reactions use fac-Ir(ppy)3 , visible light and commercially available fluoroalkyl halides and can generate valuable multisubstituted perfluoroalkylated compounds in a single step that would be challenging to prepare by other methods. Mechanistically, the photoinduced alkyl radical addition to an alkene leads to the migration of a vicinal aryl substituent from its adjacent all-carbon quaternary center with the concomitant generation of a C-radical bearing two electron-withdrawing groups that is further reduced by a hydrogen donor to complete the domino sequence.read more
Citations
More filters
Journal ArticleDOI
Radical-mediated rearrangements: past, present, and future.
TL;DR: Radical-mediated rearrangement reactions, one of the most significant transformations in organic chemistry, play an irreplaceable role in improving synthetic efficiency and molecular complexity. as discussed by the authors provides a comprehensive perspective on the area from the past to present achievements, and brings up the prospects that may inspire colleagues to develop more useful synthetic tools based on radical rearrangements.
Journal ArticleDOI
Aryl Transfer Strategies Mediated by Photoinduced Electron Transfer.
TL;DR: Radical aryl migrations are powerful techniques to forge new bonds in aromatic compounds as discussed by the authors, and the growing popularity of photoredox catalysis has led to an influx of novel strategies to initiate and control aryls migration starting from widely available radical precursors.
Journal ArticleDOI
A general electron donor–acceptor complex for photoactivation of arenes via thianthrenation
TL;DR: In this paper , photoactivation of electron donor-acceptor (EDA) complexes between arylsulfonium salts and 1,4-diazabicyclo[2.2] octane with visible light or natural sunlight was discovered.
Journal ArticleDOI
Photoinduced Metal-Free α-C(sp3)–H Carbamoylation of Saturated Aza-Heterocycles via Rationally Designed Organic Photocatalyst
Ming-Jun Yi,Huan-Xin Zhang,Teng-Fei Xiao,Ji-Hua Zhang,Zhi-Tao Feng,Li-Pu Wei,Guo-Qiang Xu,Peng-Fei Xu +7 more
TL;DR: A general strategy for the rational design of an efficient organic photocatalyst is reported and a robust method for the direct C(sp3)–H carbamoylation of saturated aza-heterocyc...
Journal ArticleDOI
Recent Advances in Photoinduced Perfluoroalkylation Using Perfluoroalkyl Halides as the Radical Precursors
TL;DR: A short review of photo-induced perfluoroalkylation methodologies and technologies can be found in this article , with a focus on photo-redox catalyst based methods.
References
More filters
Journal ArticleDOI
Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis
TL;DR: The conversion of these bench stable, benign catalysts to redox-active species upon irradiation with simple household lightbulbs represents a remarkably chemoselective trigger to induce unique and valuable catalytic processes.
Journal ArticleDOI
Organic Photoredox Catalysis
TL;DR: An overview of the basic photophysics and electron transfer theory is presented in order to provide a comprehensive guide for employing this class of catalysts in photoredox manifolds.
BookDOI
Fluorine in medicinal chemistry and chemical biology
TL;DR: This book discusses applications of fluorinated amino acids and peptides to chemical biology and pharmacology, and recent Advances in the Syntheses of Fluorinated Amino Acids.
Journal ArticleDOI
Good Partnership between Sulfur and Fluorine: Sulfur-Based Fluorination and Fluoroalkylation Reagents for Organic Synthesis
Chuanfa Ni,Mingyou Hu,Jinbo Hu +2 more
Journal ArticleDOI
Visible light-mediated atom transfer radical addition via oxidative and reductive quenching of photocatalysts.
TL;DR: Modifications of the reaction conditions allowed for the efficient ATRA of perfluoroalkyl iodides onto alkenes and alkynes utilizing the reductive quenching cycle of [Ru(bpy)(3)]Cl(2) with sodium ascorbate as the sacrificial electron donor.