Photoredox Catalysis for Building C-C Bonds from C(sp2)-H Bonds.

  title={Photoredox Catalysis for Building C-C Bonds from C(sp2)-H Bonds.},
  author={Chang-sheng Wang and Pierre H. Dixneuf and Jean‐François Soul{\'e}},
  journal={Chemical reviews},
  volume={118 16},
Transition metal-catalyzed C-H bond functionalizations have been the focus of intensive research over the last decades for the formation of C-C bonds from unfunctionalized arenes, heteroarenes, alkenes. These direct transformations provide new approaches in synthesis with high atom- and step-economy compared to the traditional catalytic cross-coupling reactions. However, such methods still suffer from several limitations including functional group tolerance and the lack of regioselectivity. In… 

Photoredox-catalyzed oxo-amination of aryl cyclopropanes

A mild photoredox-coupled ring-opening oxoamination of electronically unactivated aryl cyclopropanes with simple azaarenes and molecular oxygen is reported, which enables the expedient construction of a host of structurally diverse β-amino ketone derivatives.

Catalytic enantioselective cross dehydrogenative coupling of sp3 C-H of heterocycles.

  • S. Gandhi
  • Chemistry, Biology
    Organic & biomolecular chemistry
  • 2019
This review summarizes the progress made in the area of asymmetric cross dehydrogenative coupling of heterocycles in recent years and covers the catalytic asymmetric CDC of sp3 C-H bonds of the heterocycle with various coupling partners and illustrates the different catalytic systems employed.

Photoinduced C(sp2)-H/C(sp2)-H Cross-Coupling of Alkenes: Direct Synthesis of 1,3-Dienes.

The reaction proceeded in a highly regio- and stereoselective manner and showed broad functional group tolerance, and more than 35 substituted 1,3-dienes were synthesized with good to excellent yields through the construction of the Csp2-Csp2 bond.

Regioselective C-H Alkenylation and Unsymmetrical Bis-olefination of Heteroarene Carboxylic Acids with Ruthenium Catalysis in Water.

An efficient weak carboxylate-assisted oxidative cross-dehydrogenative C-H/C-H coupling (CDC) of heteroarenes with readily available olefins has been devised employing water as green solvent under

Superiority of Iridium Photocatalyst and Role of Quinuclidine in Selective α-C(sp3)-H Alkylation: Theoretical Insights.

A systematic study was conducted to explore the non-negligible excited-state single-electron-transfer processes and the catalytic cycle and the function of quinuclidine in the entire photocatalytic reaction was probed.

Photoinduced Arylation of Acridinium Salts: Tunable Photoredox Catalysts for C-O Bond Cleavage.

A photoinduced arylation of N-substituted acridinium salts has been developed and has exhibited a high functional group tolerance (e.g., halogen, nitrile, ketone, ester, and nitro). A broad range of

Visible light driven generation and alkyne insertion reactions of stable bis-cyclometalated Pt(iv) hydrides†

Easy accessible dimers are demonstrated as a very convenient source of Pt(C^N) subunits, which promote photooxidative C–H addition reactions with different 2-arylpyridines upon irradiation with blue light and are the first isolable Pt(iv) hydrides arising from a cyclometalation reaction.

New Trends in Enantioselective Cross-Dehydrogenative Coupling

The development of cross-dehydrogenative coupling in recent years has simplified the synthesis of many materials, as a result of facile C–H activation, which, together with its greater atom economy

Electrochemically selective double C(sp2)–X (X = S/Se, N) bond formation of isocyanides

The electrochemical reaction could exclusively occur at the isocyano part regardless of the presence of susceptible radical acceptors, such as a broad range of arenes and alkynyl moieties, even alkeny moieties.

Heterocycles via Cross Dehydrogenative Coupling: Synthesis and Functionalization

Nitrogen-containing heterocycles are a ubiquitous nature and synthetic compounds having wide spectrum of activities, which has found applications in various industrial fields. Among a variety of



Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation.

This review focuses on Rh-catalyzed methods for C-H bond functionalization, which have seen widespread success over the course of the last decade and are discussed in detail in the accompanying articles in this special issue of Chemical Reviews.

Functionalization of C–H Bonds via Metal-Catalyzed Desulfitative Coupling: An Alternative Tool for Access to Aryl- or Alkyl-Substituted (Hetero)arenes

This methodology allows the synthesis of complex molecules in only a few steps and will certainly give simpler access to a very wide variety of new biaryls or alkylated arenes useful to mat...

Functionalization of C-H Bonds by Photoredox Catalysis.

Versatile direct functionalization of inert C-H bonds including alkylation, trifluoromethylation, arylation and amidation, has been achieved using this practical strategy.

Direct (hetero)arylation: a new tool for polymer chemists.

This Account illustrates methods and present examples of DHAP reactions that involve the preparation of common homopolymers used in organic electronics, copolymers formed by activation of electron-rich and electron-deficient monomers (TPD, 1,2,4,5-tetrafluorobenzene, 2,2'-bithiazole).

Beyond directing groups: transition-metal-catalyzed C-H activation of simple arenes.

In this review, recent advances in the emerging field of non-chelate-assisted C-H activation are discussed, highlighting some of the most intriguing and inspiring examples of induction of reactivity and selectivity.

Eco-friendly solvents for palladium-catalyzed desulfitative C-H bond arylation of heteroarenes.

Herein, we report the Pd-catalyzed regioselective direct arylation of heteroarenes in which benzenesulfonyl chlorides are used as coupling partners through a desulfitative cross-coupling that can be

Palladium-catalyzed ligand-directed C-H functionalization reactions.

This is the first comprehensive review encompassing the large body of work in this field over the past 5 years, and will focus specifically on ligand-directed C–H functionalization reactions catalyzed by palladium.

Direct C-H Cyanation of Arenes via Organic Photoredox Catalysis.

The construction of aromatic nitriles via direct C-H functionalization using an acridinium photoredox catalyst and trimethylsilyl cyanide under an aerobic atmosphere is disclosed.

Merging Visible Light Photoredox Catalysis with Metal Catalyzed C–H Activations: On the Role of Oxygen and Superoxide Ions as Oxidants

The first successful endeavors to address the above challenges are described by combining visible light photoredox catalysis with different ruthenium, rhodium, or palladium catalyzed C–H activations, providing many new opportunities for further explorations in the field of C-H functionalization.

Visible Light Mediated Photoredox Catalytic Arylation Reactions.

Photoredox catalytic C-H arylation reactions are valuable alternatives to metal catalyzed reactions, have an excellent functional group tolerance, could potentially avoid metal containing catalysts, and use visible light as a traceless reagent for the activation of arylating reagents.