Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes.

The preparation of urea by Wöhler constituted a landmark achievement in organic chemistry, and it laid the ground for the early days of target-oriented organic synthesis.1 Since then, significant progress has been achieved in this discipline; many powerful single bond forming reactions and asymmetric variants have been developed. These discoveries have paved the way for the stereoselective assembly of complex organic molecules, a task deemed inconceivable by early practitioners. A great many strategies were invented by chemists in order to facilitate the synthesis of complex natural products.2 One avenue in emulating nature’s efficiency would * To whom correspondence should be addressed. E-mail: dennis.hall@ ualberta.ca. † Novartis Institute for Biomedical Research. ‡ Department of Chemistry, University of Alberta. Chem. Rev. 2009, 109, 4439–4486 4439

Natural product synthesis using multicomponent reaction strategies.

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

Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents

http://aether.cmi.ua.ac.be/artikels/Artikels%20Gitte/Artikels/Reviews/Heck-Larock%202006.pdf

Synthesis of heterocycles via palladium-catalyzed oxidative addition.

A mild procedure for the conversion of N,N-dialkylhydrazones of aromatic aldehydes to the corresponding trifluoromethyl ketohydrazones is developed based on the use of the readily available hypervalent iodine reagent (II).

Copper‐Catalyzed Trifluoromethylation of N,N‐Dialkylhydrazones

In the late 1980's, a new process based on an intramolecular palladium-mediated cyclisation coupled with a carbon-carbon bond forming reaction appeared in the literature. Since the first report, many novel ring systems have been synthesized using this methodology. The aim of this present review article is to summarise a number of synthetic applications of this new process developed over the last fifteen years.

Cyclisations involving attack of carbo- and heteronucleophiles on carbon-carbon π-bonds activated by organopalladium complexes

This review highlights the versatility of functionalized alkynes in the multicomponent construction of polysubstituted furan and pyrrole derivatives.

Functionalized acetylenes as versatile building-blocks for the multicomponent assembling of polysubstituted furans and pyrroles

Intramolecular carbocupration reaction of unactivated alkynes bearing a stabilized nucleophile: Application to the synthesis of iridoid monoterpenes

The Cu-catalyzed direct difluoroalkylation of aldehyde hydrazones with functionalized difluoromethyl bromides is described. The reaction yields stereodefined α,α–difluoro-β-keto hydrazones under mild conditions and can be carried out at a scale that opens up the possibility of practical applications.

Didier Bouyssi

Papers

Copper‐Catalyzed Trifluoromethylation of N,N‐Dialkylhydrazones

Cyclisations involving attack of carbo- and heteronucleophiles on carbon-carbon π-bonds activated by organopalladium complexes

Functionalized acetylenes as versatile building-blocks for the multicomponent assembling of polysubstituted furans and pyrroles

Intramolecular carbocupration reaction of unactivated alkynes bearing a stabilized nucleophile: Application to the synthesis of iridoid monoterpenes

C–H Difluoroalkylation of Aldehyde Hydrazones with Functionalized Difluoromethyl Bromides under Copper Catalysis