Literature DB >> 22832549

Palladium-catalyzed, pyrrolidine-mediated arylmethylation of ketones and aldehydes with coumarinyl(methyl) acetates.

Kalicharan Cattopadhyay1, Antonio Recio, Jon A Tunge.   

Abstract

We report the palladium-catalyzed, pyrrolidine-mediated α-benzylation of enamines generated from aldehydes and ketones. The method allows for direct coupling of medicinally relevant coumarin moieties with aldehydes and ketones in good yield under mild conditions. The reaction is believed to proceed via a Pd-π-benzyl complex generated from (coumarinyl)methyl acetates.

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Year:  2012        PMID： 22832549      PMCID： PMC3443958          DOI： 10.1039/c2ob25962a

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  51 in total

Review 1.  Coumarins in polymers: from light harvesting to photo-cross-linkable tissue scaffolds.

Authors:  Scott R Trenor; Allan R Shultz; Brian J Love; Timothy E Long
Journal:  Chem Rev       Date:  2004-06       Impact factor: 60.622

2.  Synthesis and biological evaluation of novel angularly fused polycyclic coumarins.

Authors:  Imtyaz A Khan; Manohar V Kulkarni; M Gopal; M S Shahabuddin; Chung-Ming Sun
Journal:  Bioorg Med Chem Lett       Date:  2005-08-01       Impact factor: 2.823

Review 3.  Pharmacogenomics: its role in re-establishing coumarin as treatment for lymphedema.

Authors:  Nicholas Farinola; Neil Piller
Journal:  Lymphat Res Biol       Date:  2005       Impact factor: 2.589

4.  Design, synthesis, and biological evaluation of imidazolyl derivatives of 4,7-disubstituted coumarins as aromatase inhibitors selective over 17-α-hydroxylase/C17-20 lyase.

Authors:  Angela Stefanachi; Angelo D Favia; Orazio Nicolotti; Francesco Leonetti; Leonardo Pisani; Marco Catto; Christina Zimmer; Rolf W Hartmann; Angelo Carotti
Journal:  J Med Chem       Date:  2011-02-22       Impact factor: 7.446

Review 5.  Coumarins.

Authors:  A Estévez-Braun; A G González
Journal:  Nat Prod Rep       Date:  1997-10       Impact factor: 13.423

6.  Palladium-catalyzed C3-benzylation of indoles.

Authors:  Ye Zhu; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2011-12-09       Impact factor: 15.419

7.  Decarboxylative benzylations of alkynes and ketones.

Authors:  Robert R P Torregrosa; Yamuna Ariyarathna; Kalicharan Chattopadhyay; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2010-07-14       Impact factor: 15.419

8.  Chemical constituents of Calophyllum brasiliense. 2. Structure of three new coumarins and cancer chemopreventive activity of 4-substituted coumarins.

Authors:  Chihiro Ito; Masataka Itoigawa; Yoshitaka Mishina; Valdir Cechinel Filho; Fumio Enjo; Harukuni Tokuda; Hoyoku Nishino; Hiroshi Furukawa
Journal:  J Nat Prod       Date:  2003-03       Impact factor: 4.050

9.  Synthesis and biological evaluation of novel coumarin-based inhibitors of Cdc25 phosphatases.

Authors:  Sergio Valente; Emilie Bana; Elodie Viry; Denyse Bagrel; Gilbert Kirsch
Journal:  Bioorg Med Chem Lett       Date:  2010-08-03       Impact factor: 2.823

10.  Stereocontrolled alkylative construction of quaternary carbon centers.

Authors:  David A Kummer; William J Chain; Marvin R Morales; Olga Quiroga; Andrew G Myers
Journal:  J Am Chem Soc       Date:  2008-09-13       Impact factor: 15.419
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  3 in total

1.  Synergistic palladium/enamine catalysis for asymmetric hydrocarbon functionalization of unactivated alkenes with ketones.

Authors:  Chiyu Wei; Xiaohan Ye; Qingyu Xing; Yong Hu; Yan Xie; Xiaodong Shi
Journal:  Org Biomol Chem       Date:  2019-06-25       Impact factor: 3.876

2.  Additive-Free Pd-Catalyzed α-Allylation of Imine-Containing Heterocycles.

Authors:  Marko Kljajic; Johannes G Puschnig; Hansjörg Weber; Rolf Breinbauer
Journal:  Org Lett       Date:  2016-12-12       Impact factor: 6.005

Review 3.  The Allylic Alkylation of Ketone Enolates.

Authors:  Lukas Junk; Uli Kazmaier
Journal:  ChemistryOpen       Date:  2020-09-10       Impact factor: 2.630
  3 in total

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