Journal ArticleDOI
Palladium-Catalyzed Cycloisomerizations of (Z)-1-Iodo-1,6-dienes: Iodine Atom Transfer and Mechanistic Insight to Alkyl Iodide Reductive Elimination
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A palladium-catalyzed iodine atom transfer cycloisomerization of (Z)-1-iodo-1,6-diene has been developed, which provides a facile method to construct six-memebered heterocycles bearing an alkyl iodide group.Abstract:
A palladium-catalyzed iodine atom transfer cycloisomerization of (Z)-1-iodo-1,6-diene has been developed, which provides a facile method to construct six-memebered heterocycles bearing an alkyl iodide group. The ligand screening shows that both the type and the quantity of ligand impose significant influences on this transformation, and the combination of 30 mol % 1,1'-bis(diphenylphosphino)ferrocene (DPPF) and 10 mol % Pd(OAc)(2) is the optimal choice. The catalytic cycle, consisting of oxidative addition of Pd(0) to vinyl iodide, intramolecular alkene insertion, and alkyl iodide reductive elimination, has been proposed and eventually supported by convincing evidence from a series of control experiments. More importantly, these control experiments disclose some features of the event of alkyl iodide reductive elimination: (1) this reductive elimination is proved to be a stereospecific process; and (2) both alkyl iodide oxidative addition and reductive elimination are not effected by a TEMPO additive. Besides its ability to undergo oxidative addition, the catalyst (palladium + DPPF) could also promote a radical transfer process. The findings described in this paper will be helpful for further development of the metal-catalyzed formation of a carbon-halide bond.read more
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Modern Transition-Metal-Catalyzed Carbon–Halogen Bond Formation
TL;DR: This Review provides comprehensive coverage of modern transition metal-catalyzed syntheses of organohalides via a diverse array of mechanisms, and focuses on the seminal stoichiometric organometallic studies which led to the corresponding catalytic processes being realized.
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Copper-Catalyzed Electrophilic Carbofunctionalization of Alkynes to Highly Functionalized Tetrasubstituted Alkenes
TL;DR: Copper catalysts enable the electrophilic carbofunctionalization of alkynes with vinyl- and diaryliodonium triflates to generate synthetically useful tetrasubstituted alkenes.
Journal ArticleDOI
Enantioselective Dearomative Difunctionalization of Indoles by Palladium-Catalyzed Heck/Sonogashira Sequence.
TL;DR: Palladium-catalyzed enantioselective dearomative arylalkynylation of N-substituted indoles, through a Heck/Sonogashira sequence, was established using a new BINOL-based phosphoramidite as the chiral ligand.
Journal ArticleDOI
Palladium-Catalyzed Carbohalogenation: Bromide to Iodide Exchange and Domino Processes
TL;DR: The first examples of domino carbohalogenation reactions have been demonstrated using both aryl iodide and aryL bromide starting materials, and complex products with multiple rings and stereogenic centers are generated in excellent yields with moderate to excellent diastereoselectivities.
Journal ArticleDOI
Recent Advances on Palladium Radical Involved Reactions
TL;DR: An up-to-date overview of catalytic methodologies involving palladium radical intermediates, which are sorted into two categories: (i) Pd(I)/(III)-mediated reactions are generally conducted through a single electron transfer process, leading to so-called Palladium radical involved reactions as discussed by the authors.
References
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Palladium-Catalyzed Ligand-Directed C−H Functionalization Reactions
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Journal ArticleDOI
Modern Synthetic Methods for Copper‐Mediated C(aryl) ? O, C(aryl) ? N, and C(aryl) ? S Bond Formation
Steven V. Ley,Andrew Thomas +1 more
TL;DR: In this article, the authors highlight the recent developments in the copper-mediated (both stoichiometric and catalytic) reactions of aryl boronic acids as reaction partners in both O- and N-arylation.
Journal ArticleDOI
Biaryl Phosphane Ligands in Palladium‐Catalyzed Amination
TL;DR: The application ofadium-catalyzed amination reactions of aryl halides in C-N cross-coupling reactions in the synthesis of heterocycles and pharmaceuticals, in materials science, and in natural product synthesis is discussed.
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