Literature DB >> 31162769

Regioselective Synthesis of Fused Furans by Decarboxylative Annulation of α,β-Alkenyl Carboxylic Acid with Cyclic Ketone: Synthesis of Di-Heteroaryl Derivatives.

Soumitra Agasti1, Tapas Pal1, Tapas Kumar Achar1, Siddhartha Maiti2, Debasis Pal1, Smita Mandal1, Kishan Daud1, Goutam Kumar Lahiri1, Debabrata Maiti1.   

Abstract

α,β-Alkenyl carboxylic acids undergo CuII -mediated decarboxylative annulation reactions with aliphatic cyclic ketones to provide synthetically valuable di-heterocycles. The annulation process tolerates a variety of aliphatic ketones and heterocyclic alkenyl carboxylic acids, producing substituted fused furan derivatives with complete regioselectivity. The current protocol offers a synthetically applicable pathway to construct a variety of oligo-heterocycles through Cu-mediated single-electron transfer and decarboxylation. Notably, synthesis of relatively inaccessible di-heterocycles has been achieved successfully using this protocol.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  annulations; copper; heteroarenes; radicals

Year:  2019        PMID: 31162769     DOI: 10.1002/anie.201906264

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  5 in total

1.  Synthesis of functionalized tetrahydropyrans via cascade cycloaddition involving silyloxyallyl cation intermediates.

Authors:  Fatimat O Badmus; Joshua A Malone; Frank R Fronczek; Rendy Kartika
Journal:  Chem Commun (Camb)       Date:  2020-04-03       Impact factor: 6.222

2.  Bimetallic Cooperative Catalysis for Decarbonylative Heteroarylation of Carboxylic Acids via C-O/C-H Coupling.

Authors:  Chengwei Liu; Chong-Lei Ji; Tongliang Zhou; Xin Hong; Michal Szostak
Journal:  Angew Chem Int Ed Engl       Date:  2021-04-06       Impact factor: 15.336

3.  Palladium-catalyzed cross-coupling reaction of alkenyl aluminums with 2-bromobenzo[b]furans.

Authors:  Chang Wen; Xin Jiang; Kun Wu; Ruiqiang Luo; Qinghan Li
Journal:  RSC Adv       Date:  2020-05-22       Impact factor: 4.036

4.  BF3·Et2O-Mediated annulation of α-keto acids with aliphatic ketones for the synthesis of γ-hydroxy-butenolides and γ-alkylidene-butenolides.

Authors:  Zhenfeng Cheng; Qingyun Gu; Yushan Xie; Yanan Zhang; Xiaobao Zeng
Journal:  RSC Adv       Date:  2022-08-25       Impact factor: 4.036

5.  Photocatalytic synthesis of tetra-substituted furans promoted by carbon dioxide.

Authors:  Ya-Ming Tian; Huaiju Wang; Burkhard König
Journal:  Chem Sci       Date:  2021-12-06       Impact factor: 9.825

  5 in total

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