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      Recent advances in visible-light-driven organic reactions

      1 , 2
      National Science Review
      Oxford University Press (OUP)

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          Abstract

          In recent years, visible-light-driven organic reactions have been experiencing a significant renaissance in response to topical interest in environmentally friendly green chemical synthesis. The transformations using inexpensive, readily available visible-light sources have come to the forefront in organic chemistry as a powerful strategy for the activation of small molecules. In this review, we focus on recent advances in the development of visible-light-driven organic reactions, including aerobic oxidation, hydrogen-evolution reactions, energy-transfer reactions and asymmetric reactions. These key research topics represent a promising strategy towards the development of practical, scalable industrial processes with great environmental benefits.

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          Merging photoredox catalysis with organocatalysis: the direct asymmetric alkylation of aldehydes.

          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 alpha-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.
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            Enantioselective alpha-trifluoromethylation of aldehydes via photoredox organocatalysis.

            The first enantioselective, organocatalytic alpha-trifluoromethylation and alpha-perfluoroalkylation of aldehydes have been accomplished using a readily available iridium photocatalyst and a chiral imidazolidinone catalyst. A range of alpha-trifluoromethyl and alpha-perfluoroalkyl aldehydes were obtained from commercially available perfluoroalkyl halides with high efficiency and enantioselectivity. The resulting alpha-trifluoromethyl aldehydes were subsequently shown to be versatile precursors for the construction of a variety of enantioenriched trifluoromethylated building blocks.
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              THE PHOTOCHEMISTRY OF THE FUTURE.

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                Author and article information

                Journal
                National Science Review
                Oxford University Press (OUP)
                2095-5138
                2053-714X
                May 2017
                May 01 2017
                April 08 2017
                May 2017
                May 01 2017
                April 08 2017
                : 4
                : 3
                : 359-380
                Affiliations
                [1 ]State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China
                [2 ]Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, China
                Article
                10.1093/nsr/nwx039
                e492b8eb-0cad-4c7f-9592-843a49c82ade
                © 2017

                http://creativecommons.org/licenses/by/4.0/

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