Literature DB >> 27189811

Rhodium(I)-Catalyzed Benzannulation of Heteroaryl Propargylic Esters: Synthesis of Indoles and Related Heterocycles.

Xiaoxun Li1, Haibo Xie1, Xiaoning Fu2, Ji-Tian Liu1, Hao-Yuan Wang1, Bao-Min Xi3, Peng Liu4, Xiufang Xu5, Weiping Tang6,7.   

Abstract

A de novo synthesis of a benzene ring allows for the preparation of a diverse range of heterocycles including indoles, benzofurans, benzothiophenes, carbazoles, and dibenzofurans from simple heteroaryl propargylic esters using a unified carbonylative benzannulation strategy. Multiple substituents can be easily introduced to the C4-C7 positions of indoles and related heterocycles.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  annulation; carbonylation; catalysis; indoles; rhodium

Year:  2016        PMID： 27189811      PMCID： PMC4945426          DOI： 10.1002/chem.201602088

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  32 in total

Review 1.  Progress in palladium-based catalytic systems for the sustainable synthesis of annulated heterocycles: a focus on indole backbones.

Authors:  Mélanie Platon; Régine Amardeil; Laurent Djakovitch; Jean-Cyrille Hierso
Journal:  Chem Soc Rev       Date:  2012-03-26       Impact factor: 54.564

2.  Recent advances in indole syntheses: new routes for a classic target.

Authors:  Rubén Vicente
Journal:  Org Biomol Chem       Date:  2011-07-21       Impact factor: 3.876

3.  Effect of ester on rhodium-catalyzed intermolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes and alkynes.

Authors:  Casi M Schienebeck; Patrick J Robichaux; Xiaoxun Li; Lianqing Chen; Weiping Tang
Journal:  Chem Commun (Camb)       Date:  2013-04-04       Impact factor: 6.222

4.  Recent advances in dearomatization of heteroaromatic compounds.

Authors:  Qiuping Ding; Xiaoli Zhou; Renhua Fan
Journal:  Org Biomol Chem       Date:  2014-07-21       Impact factor: 3.876

5.  Catalytic transmetalation from group 6 Fischer carbene complexes: an emerging powerful tool in organic synthesis.

Authors:  Mar Gómez-Gallego; María José Mancheño; Miguel A Sierra
Journal:  Acc Chem Res       Date:  2005-01       Impact factor: 22.384

6.  Palladium-catalyzed aerobic dehydrogenation of substituted cyclohexanones to phenols.

Authors:  Yusuke Izawa; Doris Pun; Shannon S Stahl
Journal:  Science       Date:  2011-06-09       Impact factor: 47.728

7.  Rh-catalyzed [5+1] and [4+1] cycloaddition reactions of 1,4-enyne esters with CO: a shortcut to functionalized resorcinols and cyclopentenones.

Authors:  Takahide Fukuyama; Yuko Ohta; Célia Brancour; Kazusa Miyagawa; Ilhyong Ryu; Anne-Lise Dhimane; Louis Fensterbank; Max Malacria
Journal:  Chemistry       Date:  2012-04-13       Impact factor: 5.236

8.  Transfer of chirality in the rhodium-catalyzed intramolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes (ACEs) and alkynes: synthesis of enantioenriched bicyclo[5.3.0]decatrienes.

Authors:  Xing-Zhong Shu; Casi M Schienebeck; Wangze Song; Ilia A Guzei; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-21       Impact factor: 15.336

9.  Cross-coupling reactions of aryl pivalates with boronic acids.

Authors:  Kyle W Quasdorf; Xia Tian; Neil K Garg
Journal:  J Am Chem Soc       Date:  2008-10-08       Impact factor: 15.419

10.  Rhodium-Catalyzed Stereoselective Intramolecular [5 + 2] Cycloaddition of 3-Acyloxy 1,4-Enyne and Alkene.

Authors:  Xing-zhong Shu; Casi M Schienebeck; Xiaoxun Li; Xin Zhou; Wangze Song; Lianqing Chen; Ilia A Guzei; Weiping Tang
Journal:  Org Lett       Date:  2015-10-06       Impact factor: 6.005
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  1 in total

Review 1.  Rhodium-Catalyzed (5 + 2) and (5 + 1) Cycloadditions Using 1,4-Enynes as Five-Carbon Building Blocks.

Authors:  Stephanie A Blaszczyk; Daniel A Glazier; Weiping Tang
Journal:  Acc Chem Res       Date:  2019-12-10       Impact factor: 22.384
  1 in total

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