Potassium phthalimide-N-oxyl: a novel, efficient, and simple organocatalyst for the one-pot three-component synthesis of various 2-amino-4H-chromene derivatives in water

Presented herein is a comprehensive account of the electronic structure of corrole derivatives. Our knowledge in this area derives from a broad range of methods, including UV–vis–NIR absorption and MCD spectroscopies, single-crystal X-ray structure determination, vibrational spectroscopy, NMR and EPR spectroscopies, electrochemistry, X-ray absorption spectroscopy, and quantum chemical calculations, the latter including both density functional theory and ab initio multiconfigurational methods. The review is organized according to the Periodic Table, describing free-base and main-group element corrole derivatives, then transition-metal corroles, and finally f-block element corroles. Like porphyrins, corrole derivatives with a redox-inactive coordinated atom follow the Gouterman four-orbital model. A key difference from porphyrins is the much wider prevalence of noninnocent electronic structures as well as full-fledged corrole•2– radicals among corrole derivatives. The most common orbital pathways mediating ...

Electronic Structure of Corrole Derivatives: Insights from Molecular Structures, Spectroscopy, Electrochemistry, and Quantum Chemical Calculations.

Since its discovery by Christoph Hartmann and Victor Meyer in 1893, 2-iodoxybenzoic acid (IBX) has emerged as a rather ubiquitous oxidant for organic synthesis. The past decade has seen the development of a large variety of applications that go far beyond the simple oxidation of alcohols. This Review is concerned with the synthetic potential of IBX, with particular emphasis on uncommon reactivity patterns and novel fields of application.

2-Iodoxybenzoic Acid—A Simple Oxidant with a Dazzling Array of Potential Applications

This review covers the functionalization reactions of meso-arylcorroles, both at the inner core, as well as the peripheral positions of the macrocycle. Experimental details for the synthesis of all known metallocorrole types and for the N-alkylation reactions are presented. Key peripheral functionalization reactions such as halogenation, formylation, carboxylation, nitration, sulfonation, and others are discussed in detail, particularly the nucleophilic aromatic substitution and the participation of corroles in cycloaddition reactions as 2π or 4π components (covering Diels–Alder and 1,3-dipolar cycloadditions). Other functionalizations of corroles include a large diversity of reactions, namely Wittig reactions, reactions with methylene active compounds, formation of amines, amides, and imines, and metal catalyzed reactions. At the final section, the reactions involving oxidation and ring expansion of the corrole macrocycle are described comprehensively.

Strategies for Corrole Functionalization.

This review describes the known electrochemistry of corroles in nonaqueous media from 1980 until the present. The outline of the review is grouped according to the periodic table, proceeding from left to right, describing first monomeric free-base derivatives and then transition-metal compounds, followed by main-group corroles, before ending with a brief description of lanthanide and actinide corroles. Many similarities exist between the redox properties of metallocorroles and metalloporphyrins, but there are also many differences due, in part, to the different charges of the two conjugated macrocycles and the noninnocence of the corrole ligand in a variety of compounds. One part of this review will focus on describing redox behavior as a function of metal ion and axial ligands, while another will focus on how changes in structure of the macrocycle are associated with changes in redox behavior. It is hoped that this review will answer the majority of the readers’ questions as to what has been electrochemi...

Electrochemistry of Corroles in Nonaqueous Media

Cerium(III) Chloride–Catalyzed One-Pot Synthesis of Tetrahydrobenzo[b]pyrans

Chelation-controlled reduction: an enantioselective synthesis of (−)-tarchonanthuslactone

Application of the Cosford cross-coupling protocol for the stereoselective synthesis of (R)-(+)-goniothalamin, (R)-(+)-kavain and (S)-(+)-7,8-dihydrokavain

Kolanu Sudhakar

Papers

Cerium(III) Chloride–Catalyzed One-Pot Synthesis of Tetrahydrobenzo[b]pyrans

Chelation-controlled reduction: an enantioselective synthesis of (−)-tarchonanthuslactone

Application of the Cosford cross-coupling protocol for the stereoselective synthesis of (R)-(+)-goniothalamin, (R)-(+)-kavain and (S)-(+)-7,8-dihydrokavain

Corrole dyes for dye-sensitized solar cells: The crucial role of the dye/semiconductor energy level alignment

CeCl3·7H2O-Catalyzed One-Pot Synthesis of Hantzsch 1,4-Dihydropyridines at Room Temperature