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Halomethyllithium Carbenoids: Versatile Reagents for the Homologation of Electrophilic Carbon Units

Vittorio Pace A
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A Department of Drug and Natural Product Synthesis, University of Vienna, Althanstrasse 14, 1090 Vienna, Austria. Email: vpace@farm.ucm.es




Vittorio Pace received a degree in Pharmacy from the University of Perugia (Italy) in 2005 and an MSc in Drug Design and Development from the University of Pavia (Italy) in 2008. He obtained a PhD in Chemistry under the guidance of Professor A. R. Alcántara at the Complutense University of Madrid (2010). He then undertook postdoctoral training at the University of Vienna (Austria) with Professor W. Holzer and at the University of Manchester (UK) with Professor D. J. Procter. In October 2013, he moved to the University of Stockholm (Sweden) for a third postdoctoral position with Professor B. Olofsson.

Australian Journal of Chemistry 67(2) 311-313 https://doi.org/10.1071/CH13416
Submitted: 10 August 2013  Accepted: 17 October 2013   Published: 28 November 2013



26 articles found in Crossref database.

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Chemical Communications. 2016 52(12). p.2639
Homologation Reactions (2023)
Ielo Laura, Miele Margherita, Pillari Veronica, Castoldi Laura, Pace Vittorio
Isocyanates and isothiocyanates as versatile platforms for accessing (thio)amide-type compounds
Pace Vittorio, Monticelli Serena, de la Vega-Hernández Karen, Castoldi Laura
Organic & Biomolecular Chemistry. 2016 14(33). p.7848
Homologation Reactions (2023)
Kimura Tsutomu, Sekiguchi Koto
Chemoselective Addition of Halomethyllithiums to Functionalized Isatins:A Straightforward Access to Spiro‐Epoxyoxindoles
Pace Vittorio, Castoldi Laura, Mamuye Ashenafi Damtew, Langer Thierry, Holzer Wolfgang
Advanced Synthesis & Catalysis. 2016 358(2). p.172
Modular and Chemoselective Strategy for Accessing (Distinct) α,α‐Dihaloketones from Weinreb Amides and Dihalomethyllithiums
Touqeer Saad, Senatore Raffaele, Malik Monika, Urban Ernst, Pace Vittorio
Advanced Synthesis & Catalysis. 2020 362(22). p.5056
External Trapping of Halomethyllithium Enabled by Flow Microreactors
Degennaro Leonardo, Fanelli Flavio, Giovine Arianna, Luisi Renzo
Advanced Synthesis & Catalysis. 2015 357(1). p.21
Chemoselective Schwartz Reagent Mediated Reduction of Isocyanates to Formamides
Pace Vittorio, de la Vega-Hernández Karen, Urban Ernst, Langer Thierry
Organic Letters. 2016 18(11). p.2750
Synthesis of stable α-fluoromethyl putative carbanions via a chemoselective reduction-monofluoromethylation sequence of diselenides under sustainable conditions
Senatore Raffaele, Malik Monika, Urban Ernst, Holzer Wolfgang, Pace Vittorio
Tetrahedron. 2021 85 p.131921
The study of the PES and the reaction mechanism between ketene and Lithium Carbenoids and the formation of cyclopropanone
Villablanca Daniel, Gazzari Sasha, Herrera Bárbara
Theoretical Chemistry Accounts. 2023 142(4).
Efficient Access to All‐Carbon Quaternary and Tertiary α‐Functionalized Homoallyl‐type Aldehydes from Ketones
Pace Vittorio, Castoldi Laura, Mazzeo Eugenia, Rui Marta, Langer Thierry, Holzer Wolfgang
Angewandte Chemie International Edition. 2017 56(41). p.12677
A practical guide for using lithium halocarbenoids in homologation reactions
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Monatshefte für Chemie - Chemical Monthly. 2018 149(7). p.1285
Highly efficient synthesis of functionalized α-oxyketones via Weinreb amides homologation with α-oxygenated organolithiums
Pace Vittorio, Murgia Irene, Westermayer Sophie, Langer Thierry, Holzer Wolfgang
Chemical Communications. 2016 52(48). p.7584
Homologation chemistry with nucleophilic α-substituted organometallic reagents: chemocontrol, new concepts and (solved) challenges
Castoldi Laura, Monticelli Serena, Senatore Raffaele, Ielo Laura, Pace Vittorio
Chemical Communications. 2018 54(50). p.6692
Increasing the Reactivity of Amides towards Organometallic Reagents: An Overview
Pace Vittorio, Holzer Wolfgang, Olofsson Berit
Advanced Synthesis & Catalysis. 2014 356(18). p.3697
Taking advantage of lithium monohalocarbenoid intrinsic α-elimination in 2-MeTHF: controlled epoxide ring-opening en route to halohydrins
Ielo Laura, Miele Margherita, Pillari Veronica, Senatore Raffaele, Mirabile Salvatore, Gitto Rosaria, Holzer Wolfgang, Alcántara Andrés R., Pace Vittorio
Organic & Biomolecular Chemistry. 2021 19(9). p.2038
Straightforward and direct access to β-seleno- amines and sulfonylamides via the controlled addition of phenylselenomethyllithium (LiCH2SePh) to imines
Senatore Raffaele, Malik Monika, Touqeer Saad, Listro Roberta, Collina Simona, Holzer Wolfgang, Pace Vittorio
Tetrahedron. 2020 76(51). p.131220
Lithium Halomethylcarbenoids: Preparation and Use in the Homologation of Carbon Electrophiles
Pace Vittorio, Holzer Wolfgang, De Kimpe Norbert
The Chemical Record. 2016 16(4). p.2061
Direct and straightforward transfer of C1 functionalized synthons to phosphorous electrophiles for accessing gem-P-containing methanes
Touqeer Saad, Ielo Laura, Miele Margherita, Urban Ernst, Holzer Wolfgang, Pace Vittorio
Organic & Biomolecular Chemistry. 2021 19(11). p.2425
Merging lithium carbenoid homologation and enzymatic reduction: A combinative approach to the HIV-protease inhibitor Nelfinavir
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Tetrahedron. 2018 74(18). p.2211
Contribution of microreactor technology and flow chemistry to the development of green and sustainable synthesis
Fanelli Flavio, Parisi Giovanna, Degennaro Leonardo, Luisi Renzo
Beilstein Journal of Organic Chemistry. 2017 13 p.520
Evidence and isolation of tetrahedral intermediates formed upon the addition of lithium carbenoids to Weinreb amides and N-acylpyrroles
Castoldi Laura, Holzer Wolfgang, Langer Thierry, Pace Vittorio
Chemical Communications. 2017 53(68). p.9498
Chemoselective Additions of Chloromethyllithium Carbenoid to Cyclic Enones: A Direct Access to Chloromethyl Allylic Alcohols
Pace Vittorio, Castoldi Laura, Holzer Wolfgang
Advanced Synthesis & Catalysis. 2014 356(8). p.1761
Consecutive C1‐Homologation / Displacement Strategy for Converting Thiosulfonates into O,S‐Oxothioacetals
Ielo Laura, Pillari Veronica, Miele Margherita, Holzer Wolfgang, Pace Vittorio
Advanced Synthesis & Catalysis. 2020 362(23). p.5444
Chemoselective efficient synthesis of functionalized β-oxonitriles through cyanomethylation of Weinreb amides
Mamuye Ashenafi Damtew, Castoldi Laura, Azzena Ugo, Holzer Wolfgang, Pace Vittorio
Organic & Biomolecular Chemistry. 2015 13(7). p.1969
Efficient Access to All‐Carbon Quaternary and Tertiary α‐Functionalized Homoallyl‐type Aldehydes from Ketones
Pace Vittorio, Castoldi Laura, Mazzeo Eugenia, Rui Marta, Langer Thierry, Holzer Wolfgang
Angewandte Chemie. 2017 129(41). p.12851

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