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

J Org Chem

†Normandie Univ, COBRA, UMR 6014 et FR 3038; Univ Rouen; INSA Rouen; CNRS, IRCOF, 1 rue Tesniére, 76821 Mont Saint Aignan Cedex, France.

Published: July 2015

AI Article Synopsis

  • A new carbonylation method using Pd catalyst allows for the coupling of various halides, including aryl and vinyl types, with N-hydroxysuccinimidyl formate as a carbon monoxide substitute.
  • High yields of up to 98% were achieved, demonstrating the effectiveness of this protocol.
  • The Pd(OAc)2/Xantphos catalyst system proved to be essential for ensuring high conversion rates to the desired NHS esters.

Article 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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Source
http://dx.doi.org/10.1021/acs.joc.5b01119DOI Listing

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