Journal ArticleDOI
Enantioselective Synthesis of Chiral-at-Cage o-Carboranes via Pd-Catalyzed Asymmetric B-H Substitution.
Ruofei Cheng,Bowen Li,Jie Wu,Jie Zhang,Zaozao Qiu,Wenjun Tang,Shu-Li You,Yong Tang,Zuowei Xie,Zuowei Xie +9 more
TLDR
This work reports an efficient method to achieve chiral-at-cage arylation of o-carboranes with high regio- and enantioselectivities by a strategy of palladium-catalyzed asymmetric intramolecular B-H arieslation and cyclization.Abstract:
Carborane cage chirality is an outstanding issue of great interest as the icosahedral carboranes have wide applications in medicinal and materials chemistry. The synthesis of optically active carborane derivatives, whose chirality is associated with the substitution patterns on the polyhedron, will open new avenues to carborane chemistry. We report herein an efficient method to achieve chiral-at-cage arylation of o-carboranes with high regio- and enantioselectivities by a strategy of palladium-catalyzed asymmetric intramolecular B–H arylation and cyclization. This represents the first example of the enantioselective reaction on carboranes, providing an efficient way for the construction of chiral-at-cage compounds with new skeletons.read more
Citations
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P-Chiral Phosphorus Ligands Based on a 2,3-Dihydrobenzo[d][1,3]oxaphosphole Motif for Asymmetric Catalysis
TL;DR: The design and development of a series of practical and efficient P-chiral bis- and monophosphorus ligands based on a 2,3-dihydrobenzo[ d][1,3]oxaphosphole motif are introduced, which make them practical and exceptional ligands for asymmetric catalysis.
Journal ArticleDOI
Controlled functionalization of o-carborane via transition metal catalyzed B–H activation
Yangjian Quan,Zuowei Xie +1 more
TL;DR: A review of recent advances in transition metal catalyzed vertex-specific BH functionalization of carbon-boron molecular clusters concludes that selection of a cage C-H bonds for functionalization is very challenging.
Journal ArticleDOI
Aggregation-Induced Electrochemiluminescence of Carboranyl Carbazoles in Aqueous Media
TL;DR: The results of cyclic voltammetry (CV) suggest that oxidation/reduction reactions take place at the carboranyl motif, and these compounds show a reductive-oxidative mechanism in contrast to other organic materials that show oxidative-reductive mechanisms.
Journal ArticleDOI
Metal-catalyzed cross-coupling chemistry with polyhedral boranes
TL;DR: This work has shown that the utility of metal-catalyzed cross-coupling can be extended to several classes of polyhedral borane including neutral and anionic carboranes, metallaboranes, and carbon-free boranes and the ability to synthesize halogenated boron-rich clusters which can serve as electrophilic cross-Coupling partners with nucleophilic substrates in the presence of a metal catalyst.
Journal ArticleDOI
Palladium-Catalyzed Selective Five-Fold Cascade Arylation of the 12-Vertex Monocarborane Anion by B-H Activation
Furong Lin,Jing-Lu Yu,Yunjun Shen,Shuo-Qing Zhang,Bernhard Spingler,Jiyong Liu,Xin Hong,Simon Duttwyler +7 more
TL;DR: A series of cage penta-arylated carboranes have been synthesized by palladium-catalyzed intermolecular coupling of the C-carboxylic acid of the monocarba- closo-dodecaborate anion with iodoarenes by direct cage B-H bond functionalization, setting a record in terms of one-pot directing group-mediated activation of inert bonds in a single molecule.
References
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Journal ArticleDOI
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TL;DR: This review describes the recent developments of highly efficient catalytic asymmetric hydrogenation of enamides, and enamines and specifically focuses on the substrates because hydrogenation is highly dependent on the substrate although the chiral metal catalysts play a significant role.
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Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C–C Bonds
TL;DR: This work states that the stereocontrolled construction of C−C bonds remains one of the foremost challenges in organic synthesis and has resulted in a paradigm shift in synthetic strategy planning.
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Boron in drug discovery: carboranes as unique pharmacophores in biologically active compounds.
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