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

Introduced to the Market in the Last Decade (2001−2011) Jiang Wang,† María Sańchez-Rosello,́‡,§ Jose ́ Luis Aceña, Carlos del Pozo,‡ Alexander E. Sorochinsky, Santos Fustero,*,‡,§ Vadim A. Soloshonok,* and Hong Liu*,† †Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, China ‡Department of Organic Chemistry, Faculty of Pharmacy, University of Valencia, Av. Vicente Andreś Estelleś, 46100 Burjassot, Valencia, Spain Laboratorio de Molećulas Orgańicas, Centro de Investigacioń Príncipe Felipe, C/ Eduardo Primo Yuf́era 3, 46012 Valencia, Spain Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizab́al 3, 20018 San Sebastian, Spain IKERBASQUE, Basque Foundation for Science, Alameda Urquijo, 36-5 Plaza Bizkaia, 48011 Bilbao, Spain Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, Murmanska Street 1, 02660 Kyiv-94, Ukraine

Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Multicomponent reactions (MCRs) are fundamentally different from two-component reactions in several aspects. Among the MCRs, those with isocyanides have developed into popular organic-chemical reactions in the pharmaceutical industry for the preparation of compound libraries of low-molecular druglike compounds. With a small set of starting materials, very large libraries can be built up within a short time, which can then be used for research on medicinal substances. Due to the intensive research of the last few years, many new backbone types have become accessible. MCRs are also increasingly being employed in the total synthesis of natural products. MCRs and especially MCRs with isocyanides offer many opportunities to attain new reactions and basic structures. However, this requires that the chemist learns the “language” of MCRs, something that this review wishes to stimulate.

Multicomponent Reactions with Isocyanides.

s, or keywords if they used Heck-type chemistry in their syntheses, because it became one of basic tools of organic preparations, a natural way to

http://aether.cmi.ua.ac.be/artikels/Artikels%20Gitte/Artikels/Reviews/Heck%20reactie%20Beletskaya%20%20Chem.%20Rev.%20003009.pdf

The heck reaction as a sharpening stone of palladium catalysis.

Catalytic dehydrogenative cross-coupling: forming carbon-carbon bonds by oxidizing two carbon-hydrogen bonds

Catalytic asymmetric synthesis of a chiral indene (97% ee) was realized by asymmetric allylic substitution of 1,3-diphenyl-2-propenyl acetate with an indenide generated from indene and cesium carbonate in the presence of a palladium catalyst coordinated with (S)-Ph-phox. The stereochemistry of the allylic substitution with the indenide was demonstrated to be net retention.

Palladium-Catalyzed Asymmetric Allylic Alkylation with an Indenide.

X-ray crystallographic studies on π-allylpalladium complexes coordinated with a chiral phosphine–olefin ligand (−)-1b demonstrate that the phosphine ligand shows a larger trans-influence than the π-bound olefin. The palladium/chiral phosphine–olefin complex efficiently catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate with 96% enantioselectivity.

Palladium/Chiral Phosphine‐Olefin Complexes: X‐Ray Crystallographic Analysis and the Use in Catalytic Asymmetric Allylic Alkylation.

Reaction of 1,4-diacetoxy-cis-2-butene (1a) with 2-(benzylamino)ethanol (2a) was catalyzed by a palladium complex (5 mol %) coordinated with (R)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl to give optically active (R)-4-benzyl-2-vinylmorpholine (3a) of up to 65% ee. Optically active 1,4-bis-(p-tolylsulfonyl)-2-vinylpiperazine (7a) (60% ee) was also obtained from 1,4-dicarbomethoxy-2-butene (1b) and 1,2-bis[p-tolylsulfonyl)amino]ethane (6a) in a similar manner. This cyclization proceeds through a tandem allylic substitution via π-allylpalladium intermediates. The palladium-catalyzed reaction with 2-amino-1,3-propanediols 17 gave 2-vinyl-5-(hydroxymethyl)morpholines of up to 73% ee

Catalytic Asymmetric Construction of Morpholines and Piperazines by Palladium-Catalyzed Tandem Allylic Substitution Reactions.

A series of amphiphilic resin-supported MOP ligands PEP-MOP were prepared on a polyethylene glycol-polystyrene graft copolymer. Palladium complexes of PEP-MOP were found to be effective as catalysts for the asymmetric substitution of 1,3-diphenyl-2-propenyl acetate with 3-methyl-2,4-pentanedione in aqueous K2CO3 to give 1,3-diphenyl-4-acetyl-4-methyl-1-hexen-5-one of up to 81% ee.

Palladium-Catalyzed Asymmetric Allylic Substitution in Aqueous Media Using Amphiphilic Resin-Supported MOP Ligands.

Palladium-Catalyzed Asymmetric Hydroalkenylation of Norbornene.

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