251
views
0
recommends
+1 Recommend
0 collections
    1
    shares
      • Record: found
      • Abstract: found
      • Article: not found

      Photoredox Catalysis in Organic Chemistry

      review-article
      , ,
      The Journal of Organic Chemistry
      American Chemical Society

      Read this article at

      ScienceOpenPublisherPMC
      Bookmark
          There is no author summary for this article yet. Authors can add summaries to their articles on ScienceOpen to make them more accessible to a non-specialist audience.

          Abstract

          In recent years, photoredox catalysis has come to the forefront in organic chemistry as a powerful strategy for the activation of small molecules. In a general sense, these approaches rely on the ability of metal complexes and organic dyes to convert visible light into chemical energy by engaging in single-electron transfer with organic substrates, thereby generating reactive intermediates. In this Perspective, we highlight the unique ability of photoredox catalysis to expedite the development of completely new reaction mechanisms, with particular emphasis placed on multicatalytic strategies that enable the construction of challenging carbon–carbon and carbon–heteroatom bonds.

          Related collections

          Most cited references115

          • Record: found
          • Abstract: found
          • Article: not found

          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.
            Bookmark
            • Record: found
            • Abstract: found
            • Article: not found

            Towards mild metal-catalyzed C-H bond activation.

            Functionalizing traditionally inert carbon-hydrogen bonds represents a powerful transformation in organic synthesis, providing new entries to valuable structural motifs and improving the overall synthetic efficiency. C-H bond activation, however, often necessitates harsh reaction conditions that result in functional group incompatibilities and limited substrate scope. An understanding of the reaction mechanism and rational design of experimental conditions have led to significant improvement in both selectivity and applicability. This critical review summarizes and discusses endeavours towards the development of mild C-H activation methods and wishes to trigger more research towards this goal. In addition, we examine select examples in complex natural product synthesis to demonstrate the synthetic utility of mild C-H functionalization (84 references). This journal is © The Royal Society of Chemistry 2011
              Bookmark
              • Record: found
              • Abstract: found
              • Article: not found

              Dual catalysis. Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis.

              The routine application of C(sp3)-hybridized nucleophiles in cross-coupling reactions remains an unsolved challenge in organic chemistry. The sluggish transmetalation rates observed for the preferred organoboron reagents in such transformations are a consequence of the two-electron mechanism underlying the standard catalytic approach. We describe a mechanistically distinct single-electron transfer-based strategy for the activation of organoboron reagents toward transmetalation that exhibits complementary reactivity patterns. Application of an iridium photoredox catalyst in tandem with a nickel catalyst effects the cross-coupling of potassium alkoxyalkyl- and benzyltrifluoroborates with an array of aryl bromides under exceptionally mild conditions (visible light, ambient temperature, no strong base). The transformation has been extended to the asymmetric and stereoconvergent cross-coupling of a secondary benzyltrifluoroborate.
                Bookmark

                Author and article information

                Journal
                J Org Chem
                J. Org. Chem
                jo
                joceah
                The Journal of Organic Chemistry
                American Chemical Society
                0022-3263
                1520-6904
                01 August 2016
                19 August 2016
                : 81
                : 16 , Photocatalysis
                : 6898-6926
                Affiliations
                [1]Merck Center for Catalysis at Princeton University , Princeton, New Jersey 08544, United States
                Author notes
                Article
                10.1021/acs.joc.6b01449
                4994065
                27477076
                8a8a0fe2-3d8f-49cc-8952-785fcb923556
                Copyright © 2016 American Chemical Society

                This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.

                History
                : 17 June 2016
                Categories
                Perspective
                Custom metadata
                jo6b01449
                jo-2016-01449t

                Organic & Biomolecular chemistry
                Organic & Biomolecular chemistry

                Comments

                Comment on this article