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.

Enantioselective 1,3‐Dipolar Cycloaddition of Nitrones with Ethyl Vinyl Ether: The Difference between Brønsted and Lewis Acid Catalysis

Enantioselective Epoxidation of Allylic Alcohols by a Chiral Complex of Vanadium: An Effective Controller System and a Rational Mechanistic Model

Recent Advances in Asymmetric Nitroso Diels–Alder Reactions

In the presence of 20 mol% of a chiral (acyloxy)borane (CAB) complex prepared from (2R,3R)-2-O(2,6-diisopropoxybenzoyl)tartaric acid and borane-tetrahydrofuran, various allyltrimethylsilanes react with achiral aldehydes to afford the corresponding homoallylic alcohols in good yields with high diastereo- and enantioselectivities. Furthermore, the reactivity of allylation can be improved without reducing the enantioselectivity by using 10-20 mol% of the CAB complex prepared from 3,5-bis(trifluoromethyl)phenylboronic acid and chiral tartaric acid derivative. The observed selectivities and re-face attack of nucleophiles on the carbonyl carbons of aldehydes imply that the extended transition-state model is applicable

Hisashi Yamamoto

Papers

Enantioselective 1,3‐Dipolar Cycloaddition of Nitrones with Ethyl Vinyl Ether: The Difference between Brønsted and Lewis Acid Catalysis

Enantioselective Epoxidation of Allylic Alcohols by a Chiral Complex of Vanadium: An Effective Controller System and a Rational Mechanistic Model

Recent Advances in Asymmetric Nitroso Diels–Alder Reactions

Catalytic asymmetric aldol reactions. use of a chiral (acyloxy)borane complex as a versatile lewis acid catalyst

Bronsted Acid Assisted Chiral Lewis Acid (BLA) Catalyst for Asymmetric Diels-Alder Reaction