Literature DB >> 32227903

Vanadium-Catalyzed Oxidative Intramolecular Coupling of Tethered Phenols: Formation of Phenol-Dienone Products.

Philip H Gilmartin1, Marisa C Kozlowski1.   

Abstract

A mild and efficient method for the vanadium-catalyzed intramolecular coupling of tethered free phenols is described. The corresponding phenol-dienone products are prepared directly in good yields with low catalyst loadings. Electronically diverse tethered phenol precursors are well tolerated, and the catalytic method was effectively applied as the key step in syntheses of three natural products and a synthetically useful morphinan alkaloid precursor.

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Year:  2020        PMID： 32227903      PMCID： PMC7314600          DOI： 10.1021/acs.orglett.0c00577

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


  25 in total

Review 1.  Atroposelective total synthesis of axially chiral biaryl natural products.

Authors:  Gerhard Bringmann; Tanja Gulder; Tobias A M Gulder; Matthias Breuning
Journal:  Chem Rev       Date:  2010-10-12       Impact factor: 60.622

Review 2.  The biocatalytic repertoire of natural biaryl formation.

Authors:  Hülya Aldemir; René Richarz; Tobias A M Gulder
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-09       Impact factor: 15.336

3.  Cinnamylphenols from Phyllodium pulchellum.

Authors:  Chien-Chang Shen; Shr-Ting Wang; Show-Yinn Tsai; Hui-Chuan Yang; Bor-Jinn Shieh; Chien-Chih Chen
Journal:  J Nat Prod       Date:  2005-05       Impact factor: 4.050

4.  Selective Oxidative Phenol Coupling by Iron Catalysis.

Authors:  Hadas Shalit; Alina Dyadyuk; Doron Pappo
Journal:  J Org Chem       Date:  2019-01-30       Impact factor: 4.354

5.  A Regio- and Diastereoselective Anodic Aryl-Aryl Coupling in the Biomimetic Total Synthesis of (-)-Thebaine.

Authors:  Alexander Lipp; Dorota Ferenc; Christoph Gütz; Mario Geffe; Nina Vierengel; Dieter Schollmeyer; Hans J Schäfer; Siegfried R Waldvogel; Till Opatz
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-14       Impact factor: 15.336

6.  Cobalt(II)[salen]-Catalyzed Selective Aerobic Oxidative Cross-Coupling between Electron-Rich Phenols and 2-Naphthols.

Authors:  Hagai Reiss; Hadas Shalit; Vlada Vershinin; Nagnath Yadav More; Hagit Forckosh; Doron Pappo
Journal:  J Org Chem       Date:  2019-05-23       Impact factor: 4.354

7.  A new H2O2/acid anhydride system for the iodoarene-catalyzed C-C bond-forming reactions of phenols.

Authors:  Toshifumi Dohi; Yutaka Minamitsuji; Akinobu Maruyama; Satoshi Hirose; Yasuyuki Kita
Journal:  Org Lett       Date:  2008-07-11       Impact factor: 6.005

8.  Flavonoids from Dalbergia louvelii and their antiplasmodial activity.

Authors:  Naïma Beldjoudi; Lengo Mambu; Mehdi Labaïed; Philippe Grellier; David Ramanitrahasimbola; Philippe Rasoanaivo; Marie Thérèse Martin; François Frappier
Journal:  J Nat Prod       Date:  2003-11       Impact factor: 4.050

9.  Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles.

Authors:  Houng Kang; Young Eun Lee; Peddiahgari Vasu Govardhana Reddy; Sangeeta Dey; Scott E Allen; Kyle A Niederer; Paul Sung; Kirsten Hewitt; Carilyn Torruellas; Madison R Herling; Marisa C Kozlowski
Journal:  Org Lett       Date:  2017-10-12       Impact factor: 6.005

10.  Dehydrogenative Anodic C-C Coupling of Phenols Bearing Electron-Withdrawing Groups.

Authors:  Johannes L Röckl; Dieter Schollmeyer; Robert Franke; Siegfried R Waldvogel
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-19       Impact factor: 15.336
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  2 in total

1.  Catalytic Oxidative Coupling of Phenols and Related Compounds.

Authors:  Jingze Wu; Marisa C Kozlowski
Journal:  ACS Catal       Date:  2022-05-18       Impact factor: 13.700

2.  Nonconventional driving force for selective oxidative C-C coupling reaction due to concurrent and curious formation of Ag0.

Authors:  Khushboo Bhanderi; Prasanna S Ghalsasi; Katsuya Inoue
Journal:  Sci Rep       Date:  2021-01-15       Impact factor: 4.379
  2 in total

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