In this review, we highlight the use of organic photoredox catalysts in a myriad of synthetic transformations with a range of applications. This overview is arranged by catalyst class where the photophysics and electrochemical characteristics of each is discussed to underscore the differences and advantages to each type of single electron redox agent. We highlight both net reductive and oxidative as well as redox neutral transformations that can be accomplished using purely organic photoredox-active catalysts. 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.

Organic Photoredox Catalysis

N-Heterocyclic Carbenes in Late Transition Metal Catalysis

Asymmetric enamine catalysis.

Reactions that convert carbon–hydrogen (C–H) bonds into carbon–carbon (C–C) or carbon–heteroatom (C–Y) bonds are attractive tools for organic chemists, potentially expediting the synthesis of target molecules through new disconnections in retrosynthetic analysis. Despite extensive inorganic and organometallic study of the insertion of homogeneous metal species into unactivated C–H bonds, practical applications of this technology in organic chemistry are still rare. Only in the past decade have metal-catalyzed C–H functionalization reactions become more widely utilized in organic synthesis.Research in the area of homogeneous transition metal–catalyzed C–H functionalization can be broadly grouped into two subfields. They reflect different approaches and goals and thus have different challenges and opportunities. One approach involves reactions of completely unfunctionalized aromatic and aliphatic hydrocarbons, which we refer to as “first functionalization”. Here the substrates are nonpolar and hydrophobic a...

Weak coordination as a powerful means for developing broadly useful C-H functionalization reactions.

Small-molecule H-bond donors in asymmetric catalysis.

The synthesis represents a highly efficient alternative to lengthy classical aldol preparations of polypropionates.

Rapid and Stereochemically Flexible Synthesis of Polypropionates: Super‐Silyl‐Governed Aldol Cascades.

Highly Stereoselective Synthesis of β-Amino Esters via Double Stereodifferentiation

Significance: The authors reported the preparation of a new chiral biaryl P,N-ligand incorporating a five-membered electron-rich heteroaromatic. This ligand is easy to prepare and an effective catalyst for the enantioselective alkynylation of imines. Comment: In contrast to the six-membered P,Nligands, five-membered P,N-ligands are configurationally unstable. The authors have succeeded in preparing a configurationally stable five-membered P,N-ligand involving π-stacking interaction, which would offer a new, unexplored chemical diversity. O

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A Chiral Biaryl P,N-Ligand for Asymmetric Catalysis

A New Condensation of Enol Silyl Ethers with Oxime Sulfonates.

Optically active 3,3'-disilylbinaphthol derivatives are disclosed, which are represented by a general formula (I) ##STR1## (wherein, R1, R2 and R3 indicate mutually same or different lower alkyl groups and/or aromatic groups), and the steric configuration of which is R form or S form.

Hisashi Yamamoto

Papers

Rapid and Stereochemically Flexible Synthesis of Polypropionates: Super‐Silyl‐Governed Aldol Cascades.

Highly Stereoselective Synthesis of β-Amino Esters via Double Stereodifferentiation

A Chiral Biaryl P,N-Ligand for Asymmetric Catalysis

A New Condensation of Enol Silyl Ethers with Oxime Sulfonates.

Optically active 3,3'-disilylbinaphthol derivatives