The preparation, structure, and chemistry of hypervalent iodine compounds are reviewed with emphasis on their synthetic application. Compounds of iodine possess reactivity similar to that of transition metals, but have the advantage of environmental sustainability and efficient utilization of natural resources. These compounds are widely used in organic synthesis as selective oxidants and environmentally friendly reagents. Synthetic uses of hypervalent iodine reagents in halogenation reactions, various oxidations, rearrangements, aminations, C–C bond-forming reactions, and transition metal-catalyzed reactions are summarized and discussed. Recent discovery of hypervalent catalytic systems and recyclable reagents, and the development of new enantioselective reactions using chiral hypervalent iodine compounds represent a particularly important achievement in the field of hypervalent iodine chemistry. One of the goals of this Review is to attract the attention of the scientific community as to the benefits of...

Advances in Synthetic Applications of Hypervalent Iodine Compounds

10. Patented Literature 2616 10.1. Esterification 2616 10.2. Ether Formation 2619 10.2.1. Etherification without Cyclization 2619 10.2.2. Etherification with Cyclization 2624 10.3. N-Alkylation 2625 10.4. Other Reactions 2627 11. Summary and Outlook 2628 12. Note Added in Proof 2628 13. Abbreviations Used in This Review 2629 14. Acknowledgments 2629 15. Supporting Information Available 2630 16. References 2630

Mitsunobu and Related Reactions: Advances and Applications

Research and industrial interest in radical C–H activation/radical cross-coupling chemistry has continuously grown over the past few decades. These reactions offer fascinating and unconventional approaches toward connecting molecular fragments with high atom- and step-economy that are often complementary to traditional methods. Success in this area of research was made possible through the development of photocatalysis and first-row transition metal catalysis along with the use of peroxides as radical initiators. This Review provides a brief and concise overview of the current status and latest methodologies using radicals or radical cations as key intermediates produced via radical C–H activation. This Review includes radical addition, radical cascade cyclization, radical/radical cross-coupling, coupling of radicals with M–R groups, and coupling of radical cations with nucleophiles (Nu).

Recent Advances in Radical C-H Activation/Radical Cross-Coupling.

Carbon trifluoromethylation reactions of hydrocarbon derivatives and heteroarenes.

Nucleophilic phosphine catalysis has proven to be a powerful tool in organic synthesis, which can provide easy access to cyclic, bicyclic or polycyclic carbocycles and heterocycles. Owing to their comparatively strong and readily tunable nucleophilicity, phosphines can be easily tailored to efficient annulation reactions with good control over reaction selectivity. This has resulted in a tremendous increase in their scope and in a concomitant number of reports where phosphine-triggered annulation reactions occur. This tutorial review summarizes the recent achievements in this area.

Phosphine-triggered synthesis of functionalized cyclic compounds

An effective strategy for the synthesis of N-2-substituted-1,2,3-triazoles with excellent yields and regioselectivity has been developed.

Conformational Control in the Regioselective Synthesis of N-2-Substituted-1,2,3-triazoles.

On the basis of our previous studies on the antiviral mechanism against tobacco mosaic virus (TMV) and structure-activity relationship of phenanthroindolizidine alkaloids, a series of 9-substituted tylophorine derivatives targeting TMV RNA were designed, synthesized, and assessed for their anti-TMV activities. The bioassay results indicated that most of these compounds showed good in vivo anti-TMV activities, and some of them displayed higher activity than that of commercial ribavirin. Especially, the anti-TMV activities of compound 3b, 4, and 6 are 2-3 times higher than that of commercial ribavirin, according to EC50 values. In this work, we have demonstrated an effective way to design new inhibitors against plant virus and developed 9-ethoxy methyl tylophorine (4) with excellent anti-TMV activity (in vitro activity, 70.2%/500 μg/mL and 27.1%/100 μg/mL; inactivation activity, 67.7%/500 μg/mL and 30.5%/100 μg/mL; curative activity, 65.3%/500 μg/mL and 30.8%/100 μg/mL; and protection activity, 65.9%/500 μg/mL and 36.0%/100 μg/mL) as a potential plant viral inhibitor.

Target-Directed Design, Synthesis, Antiviral Activity, and SARs of 9-Substituted Phenanthroindolizidine Alkaloid Derivatives.

Synthesis of 1,4-Dicarbonyl Compounds by Visible-Light-Mediated Cross-Coupling Reactions of α-Chlorocarbonyls and Enol Acetates

Progress in photochemical and electrochemical decarboxylation has enabled the rapid construction of functionalized decarboxylated products under extremely mild conditions. The utility of these meth...

Yuxiu Liu

Papers

Conformational Control in the Regioselective Synthesis of N-2-Substituted-1,2,3-triazoles.

Target-Directed Design, Synthesis, Antiviral Activity, and SARs of 9-Substituted Phenanthroindolizidine Alkaloid Derivatives.

Synthesis of 1,4-Dicarbonyl Compounds by Visible-Light-Mediated Cross-Coupling Reactions of α-Chlorocarbonyls and Enol Acetates

Photoelectrochemical Decarboxylative C–H Alkylation of Quinoxalin-2(1H)-ones

Route Evaluation and Ritter Reaction Based Synthesis of Oxazoline Acaricide Candidates FET-II-L and NK-12