Literature DB >> 19921783

Regioselective iron-catalyzed decarboxylative allylic etherification.

Rushi Trivedi1, Jon A Tunge.   

Abstract

An anionic iron complex catalyzes the decarboxylative allylation of phenols to form allylic ethers in high yield. The allylation is regioselective rather than regiospecific. This suggests that the allylation proceeds through pi-allyl iron intermediates in contrast to related allylations of carbon nucleophiles that have been proposed to proceed via sigma-allyl complexes. Ultimately, iron catalysts have the potential to replace more expensive palladium catalysts that are typically utilized for decarboxylative couplings.

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Year:  2009        PMID: 19921783     DOI: 10.1021/ol902291z

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

1.  Deacylative allylation: allylic alkylation via retro-Claisen activation.

Authors:  Alexander J Grenning; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2011-08-24       Impact factor: 15.419

Review 2.  Transition metal-catalyzed decarboxylative allylation and benzylation reactions.

Authors:  Jimmie D Weaver; Antonio Recio; Alexander J Grenning; Jon A Tunge
Journal:  Chem Rev       Date:  2011-01-14       Impact factor: 60.622

3.  Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation.

Authors:  Alexander J Grenning; Jonathan H Boyce; John A Porco
Journal:  J Am Chem Soc       Date:  2014-08-07       Impact factor: 15.419

4.  Iron-catalysed allylation-hydrogenation sequences as masked alkyl-alkyl cross-couplings.

Authors:  Josef Bernauer; Guojiao Wu; Axel Jacobi von Wangelin
Journal:  RSC Adv       Date:  2019-10-02       Impact factor: 4.036

5.  Ruthenium-catalyzed decarboxylative C-S cross-coupling of carbonothioate: synthesis of allyl(aryl)sulfide.

Authors:  Ren-Hua Zheng; Hai-Chang Guo; Ting-Ting Chen; Qing Huang; Guo-Bo Huang; Hua-Jiang Jiang
Journal:  RSC Adv       Date:  2018-07-12       Impact factor: 3.361

  5 in total

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