Merging Photoredox Catalysis with Organocatalysis: The Direct Asymmetric Alkylation of Aldehydes
TLDR
The enantioselective intermolecular α-alkylation of aldehydes has been accomplished using an interwoven activation pathway that combines both the photoredox catalyst Ru(bpy)3Cl2 and an imidazolidinone organocatalyst.Abstract:
Photoredox catalysis and organocatalysis represent two powerful fields of molecule activation that have found widespread application in the areas of inorganic and organic chemistry, respectively. We merged these two catalysis fields to solve problems in asymmetric chemical synthesis. Specifically, the enantioselective intermolecular α-alkylation of aldehydes has been accomplished using an interwoven activation pathway that combines both the photoredox catalyst Ru(bpy)3Cl2 (where bpy is 2,2′-bipyridine) and an imidazolidinone organocatalyst. This broadly applicable, yet previously elusive, alkylation reaction is now highly enantioselective and operationally trivial.read more
Citations
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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.
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Visible light photoredox catalysis: applications in organic synthesis
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References
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Journal ArticleDOI
Ru(II) polypyridine complexes: photophysics, photochemistry, eletrochemistry, and chemiluminescence
Alberto Juris,Vincenzo Balzani,F. Barigelletti,Sebastiano Campagna,Peter Belser,A. Von Zelewsky +5 more
Journal ArticleDOI
Photophysics, photochemistry and solar energy conversion with tris(bipyridyl)ruthenium(II) and its analogues
TL;DR: In this paper, the authors presented a method for the extraction of the structure of the LPI-ARTICLE-1982-012 (LPI-2012-012) abstract from the Web of Science Record.
Journal ArticleDOI
Electron Transfer In Proteins
TL;DR: Analyses of electronic-coupling strengths suggest that the efficiency of long-range ET depends on the protein secondary structure: beta sheets appear to mediate coupling more efficiently than alpha-helical structures, and hydrogen bonds play a critical role in both.
BookDOI
Radicals in Organic Synthesis
Philippe Renaud,Mukund P. Sibi +1 more
TL;DR: In this article, the authors discuss the properties of radical chain reactions, single electron properties of radicals, and applications of radical rearrangements in total synthesis, and biomaterials.
Journal ArticleDOI
Enantioselective Organocatalysis Using SOMO Activation
T. D. Beeson,Anthony Mastracchio,Anthony Mastracchio,Jun Bae Hong,Jun Bae Hong,Kate Ashton,Kate Ashton,David W. C. MacMillan,David W. C. MacMillan +8 more
TL;DR: The concept of singly occupied molecular orbital (SOMO) activation with a highly selective α-allylation of aldehydes is demonstrated with preliminary results for enantioselective heteroarylations and cyclization/halogenation cascades.