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

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.

Domaines: Chimie

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, 2015, 80 (13), pp.6537-6544. ⟨10.1021/acs.joc.5b01119⟩. ⟨hal-02046139⟩