Literature DB >> 30351050

Pd-Catalyzed Alkene Carboheteroarylation Reactions for the Synthesis of 3-Cyclopentylindole Derivatives.

Janelle K Kirsch1, Jenna L Manske1, John P Wolfe1.   

Abstract

The Pd-catalyzed alkene carboheteroarylation of aryl and alkenyl triflate electrophiles bearing pendant alkenes with heteroaromatic nucleophiles affords substituted carbocycles with 3-indolyl or 3-pyrrolyl groups. The products are obtained in moderate to good yields, and the use of alkenyl triflate substrates produces products with high diastereoselectivities. The transformation is believed to proceed via a Friedel-Crafts-like reaction between the heteroaromatic nucleophile and an intermediate electrophilic palladium complex.

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Year:  2018        PMID： 30351050      PMCID： PMC6375689          DOI： 10.1021/acs.joc.8b02165

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  19 in total

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2.  Palladium-catalyzed synthesis of N-vinyl pyrroles and indoles.

Authors:  Mohammad Movassaghi; Alison E Ondrus
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4.  Palladium-catalyzed enantioselective C-3 allylation of 3-substituted-1H-indoles using trialkylboranes.

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Journal:  J Am Chem Soc       Date:  2006-05-17       Impact factor: 15.419

5.  Enantioselective synthesis of a highly potent selective serotonin reuptake inhibitor. An application of imidazolidinone catalysis to the alkylation of indoles with an alpha,beta-disubstituted alpha,beta-unsaturated aldehyde.

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Journal:  Org Lett       Date:  2005-08-04       Impact factor: 6.005

6.  Efficient palladium-catalyzed N-arylation of indoles.

Authors:  D W Old; M C Harris; S L Buchwald
Journal:  Org Lett       Date:  2000-05-18       Impact factor: 6.005

7.  Chemo-, regio-, and enantioselective Pd-catalyzed allylic alkylation of indolocarbazole pro-aglycons.

Authors:  Barry M Trost; Michael J Krische; Volker Berl; Ellen M Grenzer
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8.  Conformationally restricted homotryptamines. Part 7: 3-cis-(3-aminocyclopentyl)indoles as potent selective serotonin reuptake inhibitors.

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Authors:  Yongda Zhang; Bruce Z Lu; Guisheng Li; Sonia Rodriguez; Jonathan Tan; Han-Xun Wei; Jianxiu Liu; Frank Roschangar; Fei Ding; Wenyi Zhao; Bo Qu; Diana Reeves; Nelu Grinberg; Heewon Lee; Golo Heckmann; Oliver Niemeier; Michael Brenner; Youla Tsantrizos; Pierre L Beaulieu; Azad Hossain; Nathan Yee; Vittorio Farina; Chris H Senanayake
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10.  Palladium-Catalyzed Direct C3-Selective Arylation of N-Unsubstituted Indoles with Aryl Chlorides and Triflates.

Authors:  Miyuki Yamaguchi; Kohei Suzuki; Yusuke Sato; Kei Manabe
Journal:  Org Lett       Date:  2017-09-12       Impact factor: 6.005
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  2 in total

1.  Pd-Catalyzed Alkene Difunctionalization Reactions of Malonate Nucleophiles: Synthesis of Substituted Cyclopentanes via Alkene Aryl-Alkylation and Akenyl-Alkylation.

Authors:  Derick R White; Elsa M Hinds; Evan C Bornowski; John P Wolfe
Journal:  Org Lett       Date:  2019-04-25       Impact factor: 6.005

2.  Pd-Catalyzed C-C, C-N, and C-O Bond-Forming Difunctionalization Reactions of Alkenes Bearing Tethered Aryl/Alkenyl Triflates.

Authors:  Derick R White; Evan C Bornowski; John P Wolfe
Journal:  Isr J Chem       Date:  2020-01-24       Impact factor: 3.333
  2 in total

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