Dr MATTIA SILVI's Outputs (11)

Oxetane Synthesis via Alcohol C–H Functionalization (2023)
Journal Article
Paul, S., Filippini, D., Ficarra, F., Melnychenko, H., Janot, C., & Silvi, M. (2023). Oxetane Synthesis via Alcohol C–H Functionalization. Journal of the American Chemical Society, 145(29), 15688–15694. https://doi.org/10.1021/jacs.3c04891

Oxetanes are strained heterocycles with unique properties that have triggered significant advances in medicinal chemistry. However, their synthesis still presents significant challenges that limit the use of this class of compounds in practical appli... Read More about Oxetane Synthesis via Alcohol C–H Functionalization.

Polarity Transduction Enables the Formal Electronically Mismatched Radical Addition to Alkenes (2023)
Journal Article
Paul, S., Filippini, D., & Silvi, M. (2023). Polarity Transduction Enables the Formal Electronically Mismatched Radical Addition to Alkenes. Journal of the American Chemical Society, 145(5), 2773-2778. https://doi.org/10.1021/jacs.2c12699

The formation of carbon-carbon bonds via the intermolecular addition of alkyl radicals to alkenes is a cornerstone of organic chemistry and plays a central role in synthesis. However, unless specific electrophilic radicals are involved, polarity matc... Read More about Polarity Transduction Enables the Formal Electronically Mismatched Radical Addition to Alkenes.

The Conceptual Development of a Conjunctive Olefination (2022)
Journal Article
Filippini, D., & Silvi, M. (2022). The Conceptual Development of a Conjunctive Olefination. SYNLETT, https://doi.org/10.1055/a-1787-1159

We recently discovered a functional group tolerant and transition-metal-free conjunctive olefination reaction with applications in late-stage functionalization chemistry. In this Synpacts contribution, we analyze the conceptual background that has st... Read More about The Conceptual Development of a Conjunctive Olefination.

Publisher Correction: Visible light-driven conjunctive olefination (Nature Chemistry, (2022), 14, 1, (66-70), 10.1038/s41557-021-00807-x) (2021)
Journal Article
Filippini, D., & Silvi, M. (2021). Publisher Correction: Visible light-driven conjunctive olefination (Nature Chemistry, (2022), 14, 1, (66-70), 10.1038/s41557-021-00807-x). Nature Chemistry, 14(1), Article 110. https://doi.org/10.1038/s41557-021-00863-3

In the version of the article originally published, there was an error in Fig. 2d. Specifically, the first instance of what now reads as “PPh3Br” initially appeared as “PPh3BrH.” This has been corrected in the online version of the article.

Visible light-driven conjunctive olefination (2021)
Journal Article
Filippini, D., & Silvi, M. (2022). Visible light-driven conjunctive olefination. Nature Chemistry, 14(1), 66-70. https://doi.org/10.1038/s41557-021-00807-x

Carboxylic acids and aldehydes are ubiquitous in chemistry and are native functionalities in many bioactive molecules and natural products. As such, a general cross-coupling process that involves these partners would open new avenues to achieve molec... Read More about Visible light-driven conjunctive olefination.

Visible‐Light‐Driven Strain‐Increase Ring Contraction Allows the Synthesis of Cyclobutyl Boronic Esters (2020)
Journal Article
Davenport, R., Silvi, M., Noble, A., Hosni, Z., Fey, N., & Aggarwal, V. K. (2020). Visible‐Light‐Driven Strain‐Increase Ring Contraction Allows the Synthesis of Cyclobutyl Boronic Esters. Angewandte Chemie International Edition, 59(16), 6525-6528. https://doi.org/10.1002/anie.201915409

There are a limited number of ring‐contraction methodologies which convert readily available five‐membered rings into strained four‐membered rings. Here we report a photo‐induced radical‐mediated ring contraction of five‐membered‐ring alkenyl boronat... Read More about Visible‐Light‐Driven Strain‐Increase Ring Contraction Allows the Synthesis of Cyclobutyl Boronic Esters.

Radical Addition to Strained σ-Bonds Enables the Stereocontrolled Synthesis of Cyclobutyl Boronic Esters (2019)
Journal Article
Silvi, M., & Aggarwal, V. K. (2019). Radical Addition to Strained σ-Bonds Enables the Stereocontrolled Synthesis of Cyclobutyl Boronic Esters. Journal of the American Chemical Society, 141(24), 9511-9515. https://doi.org/10.1021/jacs.9b03653

While radical additions to π-bonds are well established, additions to σ-bonds are far less explored. We have found that electron deficient radicals derived from alkyl iodides under visible light irradiation add to the central strained bond of bicyclo... Read More about Radical Addition to Strained σ-Bonds Enables the Stereocontrolled Synthesis of Cyclobutyl Boronic Esters.

Enhancing the potential of enantioselective organocatalysis with light (2018)
Journal Article
Melchiorre, P., & Silvi, M. (2018). Enhancing the potential of enantioselective organocatalysis with light. Nature, 554(7690), 41-49. https://doi.org/10.1038/nature25175

© 2018 Macmillan Publishers Limited, part of Springer Nature. All rights reserved. Organocatalysis - catalysis mediated by small chiral organic molecules - is a powerful technology for enantioselective synthesis, and has extensive applications in tra... Read More about Enhancing the potential of enantioselective organocatalysis with light.

Merging Photoredox with 1,2-Metallate Rearrangements: The Photochemical Alkylation of Vinyl Boronate Complexes (2017)
Journal Article
Aggarwal, V. K., Silvi, M., & Sandford, C. (2017). Merging Photoredox with 1,2-Metallate Rearrangements: The Photochemical Alkylation of Vinyl Boronate Complexes. Journal of the American Chemical Society, 139(16), 5736-5739. https://doi.org/10.1021/jacs.7b02569

© 2017 American Chemical Society. Vinyl boronates react with electron-deficient alkyl iodides in the presence of visible light to give boronic esters in which two new C-C bonds have been created. The reaction occurs by radical addition of an electron... Read More about Merging Photoredox with 1,2-Metallate Rearrangements: The Photochemical Alkylation of Vinyl Boronate Complexes.

Visible-light excitation of iminium ions enables the enantioselective catalytic β-alkylation of enals (2017)
Journal Article
Silvi, M., Verrier, C., Rey, Y. P., Buzzetti, L., & Melchiorre, P. (2017). Visible-light excitation of iminium ions enables the enantioselective catalytic β-alkylation of enals. Nature Chemistry, 9(9), 868-873. https://doi.org/10.1038/nchem.2748

© 2017 Macmillan Publishers Limited, part of Springer Nature. All rights reserved. Chiral iminium ions - generated upon condensation of α,β-unsaturated aldehydes and amine catalysts - are used extensively by chemists to make chiral molecules in enant... Read More about Visible-light excitation of iminium ions enables the enantioselective catalytic β-alkylation of enals.

Enantioselective Organocatalytic Alkylation of Aldehydes and Enals Driven by the Direct Photoexcitation of Enamines (2015)
Journal Article
Melchiorre, P., Silvi, M., Cassani, C., Arceo, E., & Jurberg, I. D. (2015). Enantioselective Organocatalytic Alkylation of Aldehydes and Enals Driven by the Direct Photoexcitation of Enamines. Journal of the American Chemical Society, 137(19), 6120-6123. https://doi.org/10.1021/jacs.5b01662

Disclosed herein is a photo-organocatalytic enantioselective α- and γ-alkylation of aldehydes and enals, respectively, with bromomalonates. The chemistry uses a commercially available aminocatalyst and occurs under illumination by a fluorescent light... Read More about Enantioselective Organocatalytic Alkylation of Aldehydes and Enals Driven by the Direct Photoexcitation of Enamines.