Journal ArticleDOI
Reactions of metallocarbenes derived from N-sulfonyl-1,2,3-triazoles
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TLDR
This tutorial review will describe the recent advances in using N-sulfonyl-1,2,3-triazoles as precursors for the formation of metal-bound imino carbene intermediates.Abstract:
Metal-stabilized carbenes derived from diazo compounds have become broadly useful reactive intermediates for organic synthesis. This tutorial review will describe the recent advances in using N-sulfonyl-1,2,3-triazoles as precursors for the formation of metal-bound imino carbene intermediates. These intermediates undergo a variety of synthetically useful transformations, which include transannulation reactions to generate new heterocycles, cyclopropanation and subsequent ring expansions, ylide formation with subsequent rearrangements, and C–H functionalization. Furthermore, many of these transformations can be conducted with high levels of enantioselectivity by use of chiral rhodium(II) catalysts.read more
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Transition-Metal-Catalyzed Cross-Couplings through Carbene Migratory Insertion
Ying Xia,Di Qiu,Jianbo Wang +2 more
TL;DR: This review will summarize the achievements made in cross-coupling area since 2001 and identify the new organometallic species generated from migratory insertion that may undergo various transformations.
Journal ArticleDOI
Transition-Metal-Catalyzed Cleavage of C-N Single Bonds.
TL;DR: This paper presents the results of aalysis experiments conducted at the BNLMS and Nankai University with real-time measurements of the response of the H2O-O2/O2 mixture to E2O/O3 mixture.
Journal ArticleDOI
New Approaches to the Synthesis of Metal Carbenes
TL;DR: Some of the most important breakthroughs in the generation, catalytic reactions, and selectivity control of metal carbenes from non-diazo starting compounds are summarized.
Journal ArticleDOI
Generation of α-Imino Gold Carbenes through Gold-Catalyzed Intermolecular Reaction of Azides with Ynamides
TL;DR: The generation of α-imino gold carbenes via gold-catalyzed intermolecular reaction of azides and ynamides through a mechanistic rationale for this tandem reaction, especially for the observed high regioselectivity, is supported by DFT calculations.
Journal ArticleDOI
Blue light-promoted photolysis of aryldiazoacetates
TL;DR: Aryldiazoacetates can undergo photolysis under blue light irradiation at room temperature and under air in the presence of numerous trapping agents, thus providing a straighforward and general platform for their mild functionalization.
References
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Journal ArticleDOI
Cu-catalyzed azide-alkyne cycloaddition.
TL;DR: The basis for the unique properties and rate enhancement for triazole formation under Cu(1) catalysis should be found in the high ∆G of the reaction in combination with the low character of polarity of the dipole of the noncatalyzed thermal reaction, which leads to a considerable activation barrier.
Journal ArticleDOI
Copper-catalyzed azide–alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(I) acetylides
Jason E. Hein,Valery V. Fokin +1 more
TL;DR: This tutorial review examines the history of the development of the CuAAC reaction, its key mechanistic aspects, and highlights the features that make it useful to practitioners in different fields of chemical science.
Journal ArticleDOI
Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion.
Book
Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides
TL;DR: Synthesis of Alpha-Diazocarbonyl Compounds Catalysts for Metal Carbene Transformations Insertion Reactions Intermolecular Cyclopropanation and Related Addition Reactions Intramolecular cyclopropaneation and related addition Reactions Cycloaddition and Substitution Reactions with Aromatic and Heteroaromatic Compounds Generation and Reactions of Ylides from DBCs X-H InsertionReactions of DBC compounds (X = N,O,S,Se,P, Halogen) The
Journal ArticleDOI
Guiding principles for site selective and stereoselective intermolecular C–H functionalization by donor/acceptor rhodium carbenes
Huw M. L. Davies,Daniel Morton +1 more
TL;DR: This tutorial review presents a description of the controlling elements of intermolecular C-H functionalization by means of rhodium carbenes, and several examples will be shown of how this methodology can be applied to streamline the synthesis of natural products and pharmaceutical targets.