Literature DB >> 15357613

Formation of a quaternary carbon center through the Pd(0)/PhCOOH-catalyzed allylation of cyclic beta-keto esters and 1,3-diketones with alkynes.

Nitin T Patil1, Yoshinori Yamamoto.   

Abstract

Formation of a quaternary carbon center through the allylation of beta-keto esters and 1,3-diketones with alkynes is accomplished by the use of Pd(0)/benzoic acid catalyst. Reactions of various cyclic beta-keto esters and 1,3-diketones with alkynes in the presence of Pd(2)dba(3).CHCl(3) (5 mol %), PPh(3) (40 mol %), and PhCOOH (10 mol %) proceeded at 100 degrees C in toluene (5 M) to give the corresponding allylation products in high yields in a regio- and stereoselective manner. The possibility of asymmetric allylation is also discussed.

Entities:  

Year:  2004        PMID: 15357613     DOI: 10.1021/jo0490144

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


  4 in total

Review 1.  Alkynes as Electrophilic or Nucleophilic Allylmetal Precursors in Transition-Metal Catalysis.

Authors:  Alexander M Haydl; Bernhard Breit; Tao Liang; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-10       Impact factor: 15.336

2.  Tandem Rh-catalysis: decarboxylative β-keto acid and alkyne cross-coupling.

Authors:  Faben A Cruz; Zhiwei Chen; Sarah I Kurtoic; Vy M Dong
Journal:  Chem Commun (Camb)       Date:  2016-04-04       Impact factor: 6.222

3.  Catalytic asymmetric Nakamura reaction by gold(I)/chiral N,N'-dioxide-indium(III) or nickel(II) synergistic catalysis.

Authors:  Xinyue Hu; Xiaoxue Tang; Xiying Zhang; Lili Lin; Xiaoming Feng
Journal:  Nat Commun       Date:  2021-05-21       Impact factor: 14.919

4.  Monoallylation and benzylation of dicarbonyl compounds with alcohols catalysed by a cationic cobalt(iii) compound.

Authors:  Mohan Chandra Sau; Smita Mandal; Manish Bhattacharjee
Journal:  RSC Adv       Date:  2021-03-01       Impact factor: 3.361

  4 in total

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