Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/108000
Type: Artigo de periódico
Title: Evolution And Synthetic Applications Of The Heck-matsuda Reaction: The Return Of Arenediazonium Salts To Prominence
Author: Taylor J.G.
Moro A.V.
Correia C.R.D.
Abstract: This review highlights the potential and the versatility of arenediazonium salts as viable alternatives to conventional aryl halides and oxygen-based electrophiles for Pd-catalyzed Heck reactions. It also presents an overview of the field over the last decade, including some historical perspective of the Heck-Matsuda (HM) reaction with general considerations regarding reaction conditions, type of catalysts used, and the application of arenediazonium salts as reagents for the HM arylation of several types of alkenes. Throughout this review, the principal aspects related to reactivity and selectivity are discussed, and when applicable a comparison is made between the HM and the conventional Heck reactions. One-pot procedures that involve generation of the arenediazonium salt in situ from the corresponding aniline have been presented as well as some useful heterogeneous catalytic protocols. Allylic alcohols, conjugated alkenes, unsaturated heterocycles, and unactivated alkenes are capable of being arylated with arenediazonium salts by using simple catalysts such as Pd(OAc)2 or Pd2(dba)3 at room temperature in air and in benign and conventional solvents. In addition to the intramolecular variant of the HM reaction, intermolecular tandem coupling-cyclization processes have also been developed for the construction of a range of oxygen and nitrogen heterocycles. Finally, several applications towards the total synthesis of biologically active natural and nonnatural compounds are highlighted as well as the use of the HM reaction in the synthesis of new chiral, nonracemic ligands. This review highlights the synthetic potential and the versatility of arenediazonium salts as viable electrophiles for Pd-catalyzed Heck reactions. The principal aspects related to reactivity and selectivity are discussed, and when applicable a comparison is made between the Heck-Matsuda and the conventional Heck reactions. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Editor: 
Rights: fechado
Identifier DOI: 10.1002/ejoc.201001620
Address: http://www.scopus.com/inward/record.url?eid=2-s2.0-79952155959&partnerID=40&md5=4df35361ee2f4e0a0f4e0c10b91e5b34
Date Issue: 2011
Appears in Collections:Unicamp - Artigos e Outros Documentos

Files in This Item:
File SizeFormat 
2-s2.0-79952155959.pdf4.01 MBAdobe PDFView/Open


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.