Literature DB >> 19209934

Multicatalytic synthesis of alpha-pyrrolidinyl ketones via a tandem palladium(II)/indium(III)-catalyzed aminochlorocarbonylation/Friedel-Crafts acylation reaction.

Tim A Cernak1, Tristan H Lambert.   

Abstract

An oxidative carbonylation reaction that generates acid chloride functionality has been developed. Furthermore, this aminochlorocarbonylation reaction has been merged with a catalytic Friedel-Crafts acylation to produce a highly efficient tandem multicatalytic synthesis of pyrrolidinyl ketones. Significant variation of the aromatic nucleophile and substrate are shown. Two examples of incorporation of this method in triple-catalytic sequences are also demonstrated.

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Year:  2009        PMID： 19209934     DOI： 10.1021/ja809897f

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  12 in total

1.  Multicatalytic, asymmetric Michael/Stetter reaction of salicylaldehydes and activated alkynes.

Authors:  Claire M Filloux; Stephen P Lathrop; Tomislav Rovis
Journal:  Proc Natl Acad Sci U S A       Date:  2010-07-16       Impact factor: 11.205

2.  Enamine/Carbene Cascade Catalysis in the Diastereo- and Enantioselective Synthesis of Functionalized Cyclopentanones.

Authors:  Kerem E Ozboya; Tomislav Rovis
Journal:  Chem Sci       Date:  2011-09-01       Impact factor: 9.825

3.  A general approach to intermolecular carbonylation of arene C-H bonds to ketones through catalytic aroyl triflate formation.

Authors:  R Garrison Kinney; Jevgenijs Tjutrins; Gerardo M Torres; Nina Jiabao Liu; Omkar Kulkarni; Bruce A Arndtsen
Journal:  Nat Chem       Date:  2017-12-11       Impact factor: 24.427

4.  Combined oxypalladation/C-H functionalization: palladium(II)-catalyzed intramolecular oxidative oxyarylation of hydroxyalkenes.

Authors:  Rong Zhu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-11       Impact factor: 15.336

5.  Convergent Synthesis of 2H-Chromenes - a Formal [3+3] Cycloaddition by a One-pot, Three-Step Cascade.

Authors:  Kathlyn A Parker; Thomas L Mindt
Journal:  Tetrahedron       Date:  2011-12-23       Impact factor: 2.457

6.  Diethylzinc-Mediated Metalloamination-Alkylation of N, N-Dimethylhydrazinoalkenes. Catalysis of C-Zn Alkylation Using Simple Cu(I) Salts.

Authors:  Ky Mickelsen; Sean Zabawa; Tom Livinghouse
Journal:  Synlett       Date:  2017-10-12       Impact factor: 2.454

7.  Asymmetric synthesis of functionalized cyclopentanones via a multicatalytic secondary amine/N-heterocyclic carbene catalyzed cascade sequence.

Authors:  Stephen P Lathrop; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2009-09-30       Impact factor: 15.419

8.  Synthesis of tetrahydropyran/tetrahydrofuran-containing macrolides by palladium-catalyzed alkoxycarbonylative macrolactonizations.

Authors:  Yu Bai; Dexter C Davis; Mingji Dai
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-13       Impact factor: 15.336

9.  Recent developments in the use of aza-Heck cyclizations for the synthesis of chiral N-heterocycles.

Authors:  Nicholas J Race; Ian R Hazelden; Adele Faulkner; John F Bower
Journal:  Chem Sci       Date:  2017-06-20       Impact factor: 9.825

10.  Palladium catalyzed synthesis of indolizines via the carbonylative coupling of bromopyridines, imines and alkynes.

Authors:  Sébastien A Roy; José Zgheib; Cuihan Zhou; Bruce A Arndtsen
Journal:  Chem Sci       Date:  2020-12-22       Impact factor: 9.825
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