Literature DB >> 25044815

N-heterocyclic-carbene-catalyzed synthesis of 2-aryl indoles.

M Todd Hovey1, Christopher T Check, Alexandra F Sipher, Karl A Scheidt.   

Abstract

A convergent and efficient transition-metal-free catalytic synthesis of 2-aryl-indoles has been developed. The interception of a highly reactive and transient aza-ortho-quinone methide by an acyl anion equivalent generated through N-hetereocyclic carbene catalysis is central to this successful strategy. High yields and a wide scope as well as the streamlined synthesis of a kinase inhibitor are reported.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric synthesis; carbenes; cooperative effects

Mesh：

Substances：

Year:  2014        PMID： 25044815      PMCID： PMC4164393          DOI： 10.1002/anie.201405035

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


  59 in total

1.  Fischer indole synthesis with organozinc reagents.

Authors:  Benjamin A Haag; Zhi-Guang Zhang; Jin-Shan Li; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-03       Impact factor: 15.336

2.  Discovering New Reactions with N-Heterocyclic Carbene Catalysis.

Authors:  Eric M Phillips; Audrey Chan; Karl A Scheidt
Journal:  Aldrichimica Acta       Date:  2009       Impact factor: 3.667

Review 3.  Practical methodologies for the synthesis of indoles.

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4.  The azaallylic anion as a synthon for pd-catalyzed synthesis of heterocycles: domino two- and three-component synthesis of indoles.

Authors:  José Barluenga; Agustín Jiménez-Aquino; Carlos Valdés; Fernando Aznar
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 5.  Asymmetric enamine catalysis.

Authors:  Santanu Mukherjee; Jung Woon Yang; Sebastian Hoffmann; Benjamin List
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

Review 6.  Chiral dialkylaminopyridine catalysts in asymmetric synthesis.

Authors:  Ryan P Wurz
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

Review 7.  Marine indole alkaloids: potential new drug leads for the control of depression and anxiety.

Authors:  Anna J Kochanowska-Karamyan; Mark T Hamann
Journal:  Chem Rev       Date:  2010-08-11       Impact factor: 60.622

8.  Brönsted acid-catalyzed one-pot synthesis of indoles from o-aminobenzyl alcohols and furans.

Authors:  Alexey Kuznetsov; Anton Makarov; Aleksandr E Rubtsov; Alexander V Butin; Vladimir Gevorgyan
Journal:  J Org Chem       Date:  2013-11-20       Impact factor: 4.354

9.  Rhodium(III)-catalyzed arene and alkene C-H bond functionalization leading to indoles and pyrroles.

Authors:  David R Stuart; Pamela Alsabeh; Michelle Kuhn; Keith Fagnou
Journal:  J Am Chem Soc       Date:  2010-12-06       Impact factor: 15.419

10.  Indoles from simple anilines and alkynes: palladium-catalyzed C-H activation using dioxygen as the oxidant.

Authors:  Zhuangzhi Shi; Chun Zhang; Si Li; Delin Pan; Shengtao Ding; Yuxin Cui; Ning Jiao
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
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  3 in total

1.  N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

Authors:  Anna Lee; Karl A Scheidt
Journal:  Chem Commun (Camb)       Date:  2015-02-25       Impact factor: 6.222

Review 2.  Synthesis of indole derivatives as prevalent moieties present in selected alkaloids.

Authors:  Majid M Heravi; Zahra Amiri; Kosar Kafshdarzadeh; Vahideh Zadsirjan
Journal:  RSC Adv       Date:  2021-10-15       Impact factor: 4.036

3.  Azaindole synthesis through dual activation catalysis with N-heterocyclic carbenes.

Authors:  Hayden A Sharma; M Todd Hovey; Karl A Scheidt
Journal:  Chem Commun (Camb)       Date:  2016-07-01       Impact factor: 6.222
  3 in total

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