Personne : Misal Castro, Luis Carlos
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Misal Castro
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Luis Carlos
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Université Laval. Département de chimie
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ncf13688668
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Publication Accès libre Metal-free borylative dearomatization of indoles : exploring the divergent reactivity of aminoborane C–H borylation catalysts(Royal Society of Chemistry, 2018-05-07) Fontaine, Frédéric-Georges; Misal Castro, Luis Carlos; Jayaraman, Arumugam; Desrosiers, VincentWhile the dearomatization of indoles by carbon–boron bond forming reactions is new and quite promising, they are so far mainly metal-catalyzed. Here, we establish the use of metal-free catalysts in promoting such reactions in an atom-efficient way. The in situ generated ambiphilic aminoborane catalyst (1-Pip-2-BH2-C6H4)2 (Pip = piperidyl) promotes borylative dearomatization of various 1-arylsulfonyl indoles with pinacolborane in a syn addition fashion, with H and Bpin groups added respectively to the 2 and 3 positions of indoles. Catalysis proceeds with good to excellent conversion and essentially with complete regio- and diastereoselectivity. From mechanistic insights and DFT computations, we realized and established that prototypical boranes can also catalyze this borylative dearomatization.Publication Accès libre Practical and scalable synthesis of borylated heterocycles using bench-stable precursors of metal-free Lewis pair catalysts(ACS Publications, 2018-10-04) Fontaine, Frédéric-Georges; Misal Castro, Luis Carlos; Jayaraman, ArumugamA practical and scalable metal-free catalytic method for the borylation and borylative dearomatization of heteroarenes has been developed. This synthetic method uses inexpensive and conveniently synthesizable bench-stable precatalysts of the form 1-NHR₂-2-BF₃-C₆H₄, commercially and synthetically accessible heteroarenes as substrates, and pinacolborane as the borylation reagent. The preparation of several borylated heterocycles on 2 and 50 g scales was achieved under solvent-free conditions without the use of Schlenk techniques or a glovebox. A kilogram-scale borylation of one of the heteroarene substrates was also achieved using this cost-effective green methodology to exemplify the fact that our methodology can be conveniently implemented in fine chemical industries.