Literature DB >> 24047333

Palladium-catalyzed β-arylation of silyl ketene acetals and application to the synthesis of benzo-fused δ-lactones.

Sam Aspin1, Laura López-Suárez, Paolo Larini, Anne-Sophie Goutierre, Rodolphe Jazzar, Olivier Baudoin.   

Abstract

Silyl ketene acetals are shown to be competent nucleophiles in Pd-catalyzed migrative C(sp(3))-H arylations. Compared to the parent ester lithium enolates, they possess decreased reactivity but enhanced chemoselectivity. This behavior was exploited through the synthesis of valuable benzo-fused δ-lactones such as 1-isochromanones and dihydrocoumarins.

Entities:  

Year:  2013        PMID: 24047333     DOI: 10.1021/ol402398s

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


  2 in total

1.  β-C(sp(3))-H Arylation of α-Hydroxy Acid Derivatives Utilizing Amino Acid as a Directing Group.

Authors:  Tetsuya Toba; Yi Hu; Anh T Tran; Jin-Quan Yu
Journal:  Org Lett       Date:  2015-12-04       Impact factor: 6.005

2.  Pd(Quinox)-Catalyzed Allylic Relay Suzuki Reactions of Secondary Homostyrenyl Tosylates via Alkene-Assisted Oxidative Addition.

Authors:  Benjamin J Stokes; Amanda J Bischoff; Matthew S Sigman
Journal:  Chem Sci       Date:  2014-06-01       Impact factor: 9.825

  2 in total

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