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Palladium-Catalyzed Carbonylation of (Hetero)Aryl, Alkenyl and Allyl Halides by Means of N-Hydroxysuccinimidyl Formate as CO Surrogate

Anaïs Barré 1, 2 Mihaela-Liliana Tîntas 2 Florent Alix 1 Vincent Gembus 1 Cyril Papamicaël 2 Vincent Levacher 2
1 VFP Therapies Drugs : Highway to the Brain
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
Abstract : An efficient Pd-catalyzed carbonylation protocol is described for the coupling of a large panel of aryl, heteroaryl, benzyl, vinyl and allyl halides 2 with the unusual N-hydroxysuccinimidyl (NHS) formate 1 as a CO surrogate to afford the corresponding valuable NHS esters 3. High conversion to the coupling products was achieved with up to 98% yield by means of Pd(OAc)2/Xantphos catalyst system.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046139
Contributor : Madeleine Roux-Merlin <>
Submitted on : Friday, February 22, 2019 - 3:31:52 PM
Last modification on : Friday, February 5, 2021 - 3:30:05 PM

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CNRS | COMUE-NORMANDIE | UNIROUEN | INSA-ROUEN | COBRA | INC-CNRS | INSA-GROUPE | ENSICAEN | UNILEHAVRE | UNICAEN

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Anaïs Barré, Mihaela-Liliana Tîntas, Florent Alix, Vincent Gembus, Cyril Papamicaël, et al.. Palladium-Catalyzed Carbonylation of (Hetero)Aryl, Alkenyl and Allyl Halides by Means of N-Hydroxysuccinimidyl Formate as CO Surrogate. Journal of Organic Chemistry, American Chemical Society, 2015, 80 (13), pp.6537-6544. ⟨10.1021/acs.joc.5b01119⟩. ⟨hal-02046139⟩

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