Anodic benzylic C(sp3)–H amination: unified access to pyrrolidines and piperidines
نویسندگان
چکیده
منابع مشابه
Hemiaminals as substrates for sulfur ylides: direct asymmetric syntheses of functionalised pyrrolidines and piperidines.
Phenyl stabilised chiral sulfur ylides react with five-membered-ring hemiaminals to give functionalised pyrrolidines directly with high enantioselectivity. The reaction can be diverted to give piperidines instead by isolation of the intermediate epoxide and treatment with TMSOTf.
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Université Sorbonne Paris Cité (USPC), Pharmacie de Paris, UMR CNRS 8638 (COM Paris, France. E-mail: etienne.brachet parisdescartes.fr University of Regensburg Faculty of Chem Chemistry, Universitätsstraße 31, 93053 Re Université Sorbonne Paris Cité (USPC), Pharmacie de Paris, UMR CNRS 8015 (LC Paris, France † Electronic supplementary information ( and crystallographic data in CIF or 10.1039/c6...
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C-H bonds are ubiquitous structural units of organic molecules. Although these bonds are generally considered to be chemically inert, the recent emergence of methods for C-H functionalization promises to transform the way synthetic chemistry is performed. The intermolecular amination of C-H bonds represents a particularly desirable and challenging transformation for which no efficient, highly s...
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A combination of computational and experimental methods was carried out to elucidate the mechanism of palladium-catalyzed water-assisted benzylic C-H amination with N-fluorobenzenesulfonimide (NFSI), which involved the oxidative addition of Pd(II) to Pd(IV)-species as a rate-limiting step, followed by water-assisted concerted metalation-deprotonation (CMD) of the Pd(IV) complex and water-assist...
متن کاملMetal–organic layers stabilize earth-abundant metal–terpyridine diradical complexes for catalytic C–H activation† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc03537c
We report the synthesis of a terpyridine-based metal-organic layer (TPY-MOL) and its metalation with CoCl2 and FeBr2 to afford CoCl2·TPY-MOL and FeBr2·TPY-MOL, respectively. Upon activation with NaEt3BH, CoCl2·TPY-MOL catalyzed benzylic C-H borylation of methylarenes whereas FeBr2·TPY-MOL catalyzed intramolecular Csp3 -H amination of alkyl azides to afford pyrrolidines and piperidines. X-ray ab...
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ژورنال
عنوان ژورنال: Green Chemistry
سال: 2018
ISSN: 1463-9262,1463-9270
DOI: 10.1039/c8gc01411f