Jump to main content
Jump to site search


Formation of Allylated Quaternary Carbon Centers via C–O/C–O Bond Fragmentation of Oxalates and Allyl Carbonates

Abstract

Disclosed herein emphasizes Fe-promoted cross-electrophile allylation of tertiary alkyl oxalates with allyl carbonates that generates all C(sp3)-quaternary centers. The reaction involves fragmentation of tertiary alkyl oxalate C-O bonds to give tertiary alkyl radical intermediates, addition of the radicals to less hindered alkene terminals, and subsequent cleavage of the allyl C–O bonds. Allylation with 2-aryl substituted allyl carbonates was mediated by Zn/MgCl2, and Fe is used to promote the radical addition efficiency. By introduction of activated akenes, a three-component radical cascade reaction took place.

Back to tab navigation

Supplementary files

Publication details

The article was received on 10 Sep 2019, accepted on 02 Dec 2019 and first published on 02 Dec 2019


Article type: Communication
DOI: 10.1039/C9CC07072A
Chem. Commun., 2019, Accepted Manuscript

  •   Request permissions

    Formation of Allylated Quaternary Carbon Centers via C–O/C–O Bond Fragmentation of Oxalates and Allyl Carbonates

    H. Chen , Y. Ye, W. Tong, J. Fang and H. Gong, Chem. Commun., 2019, Accepted Manuscript , DOI: 10.1039/C9CC07072A

Search articles by author

Spotlight

Advertisements