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.

Le (bis-[(bromo-4 di-t-butyl-2,6)phenoxy methyl) aluminium peut etre utilise pour obtenir l'isomere (Z) alors que l'isomere (E) est produit avec le (bis-[diphenyl-2,6 phenoxy] methyl) aluminium

Organoaluminum-promoted Claisen rearrangement of allyl vinyl ethers

Catalytic asymmetric allylation of aldehydes with allylic trimethoxysilanes was achieved with the p-Tol-BINAP small middle dotAgF complex as catalyst [Eq. (a); p-Tol-BINAP=2,2'-bis(di-p-tolylphosphanyl)-1,1'-binaphthyl)]. High anti and enantioselectivities were obtained in the reaction with crotyltrimethoxysilane, irrespective of the configuration at the double bond.

Hisashi Yamamoto

Papers

Organoaluminum-promoted Claisen rearrangement of allyl vinyl ethers

Enantioselective Addition of Allylic Trimethoxysilanes to Aldehydes Catalyzed by p-Tol-BINAP small middle dotAgF.

Novel α-Amino Acid-Based Hydroxamic Acid Ligands for Vanadium-Catalyzed Asymmetric Epoxidation of Allylic Alcohols

The First Enantioselective Biomimetic Cyclization of Polyprenoids

Organoaluminum reagents of type R1R2NAlEt2 which allow regiospecific isomerization of epoxides to allylic alcohols