Photocatalytic Radical Coupling of Organoborates with α-Halogenated Electron-Poor Olefins

Marina Caldarelli; Sarah Jane Rezzi; Nicoletta Colombo; Tracey PIRALI; Gianluca Papeo

doi:10.1021/acs.joc.3c02386

Photocatalytic Radical Coupling of Organoborates with α-Halogenated Electron-Poor Olefins

Marina Caldarelli, Sarah Jane Rezzi, Nicoletta Colombo, Tracey PIRALI, Gianluca Papeo

Dipartimento di Scienze del Farmaco

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

Abstract

Herein, we report the visible-light-mediated addition of organoborates to alpha-halogenated electron-poor olefins enabled by an environmentally benign metal-free catalyst. The method accommodates a variety of boronic acid derivatives as well as alkenes and delivers the corresponding saturated alpha-halo-derivatives in up to 90% yields. The obtained products are high-value building blocks in organic synthesis, allowing for a variety of follow-up transformations.

Lingua originale	Inglese
Rivista	Journal of Organic Chemistry
Volume	89
Numero di pubblicazione	1
DOI	https://doi.org/10.1021/acs.joc.3c02386
Stato di pubblicazione	Pubblicato - 2024

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10.1021/acs.joc.3c02386

https://hdl.handle.net/11579/178882

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title = "Photocatalytic Radical Coupling of Organoborates with α-Halogenated Electron-Poor Olefins",

abstract = "Herein, we report the visible-light-mediated addition of organoborates to alpha-halogenated electron-poor olefins enabled by an environmentally benign metal-free catalyst. The method accommodates a variety of boronic acid derivatives as well as alkenes and delivers the corresponding saturated alpha-halo-derivatives in up to 90\% yields. The obtained products are high-value building blocks in organic synthesis, allowing for a variety of follow-up transformations.",

author = "Marina Caldarelli and Rezzi, \{Sarah Jane\} and Nicoletta Colombo and Tracey PIRALI and Gianluca Papeo",

year = "2024",

doi = "10.1021/acs.joc.3c02386",

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AU - Caldarelli, Marina

AU - Rezzi, Sarah Jane

AU - Colombo, Nicoletta

AU - PIRALI, Tracey

AU - Papeo, Gianluca

PY - 2024

Y1 - 2024

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AB - Herein, we report the visible-light-mediated addition of organoborates to alpha-halogenated electron-poor olefins enabled by an environmentally benign metal-free catalyst. The method accommodates a variety of boronic acid derivatives as well as alkenes and delivers the corresponding saturated alpha-halo-derivatives in up to 90% yields. The obtained products are high-value building blocks in organic synthesis, allowing for a variety of follow-up transformations.

UR - https://iris.uniupo.it/handle/11579/178882

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DO - 10.1021/acs.joc.3c02386

M3 - Article

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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Photocatalytic Radical Coupling of Organoborates with α-Halogenated Electron-Poor Olefins

Abstract

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