Literature DB >> 34231368

Friedel-Crafts-Type Reactions with Electrochemically Generated Electrophiles from Donor-Acceptor Cyclopropanes and -Butanes.

Simon Kolb1, Nils L Ahlburg1, Daniel B Werz1.   

Abstract

We describe a general electrochemical method to functionalize donor-acceptor (D-A) cyclopropanes and -butanes with arenes utilizing Friedel-Crafts-type reactivity. The catalyst-free strategy relies on the direct anodic oxidation of the strained carbocycles, which leads after C(sp3)-C(sp3) cleavage to radical cations that act as electrophiles for the arylation reaction. Broad reaction scopes in regard to cyclopropanes, cyclobutanes, and aromatic reaction partners are presented. Additionally, a plausible electrolysis mechanism is proposed.

Entities:  

Year:  2021        PMID： 34231368     DOI： 10.1021/acs.orglett.1c01890

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


  3 in total

1.  Lewis-Acid-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thioketenes.

Authors:  Grzegorz Mlostoń; Mateusz Kowalczyk; André U Augustin; Peter G Jones; Daniel B Werz
Journal:  European J Org Chem       Date:  2021-08-25

2.  Reductive opening of a cyclopropane ring in the Ni(II) coordination environment: a route to functionalized dehydroalanine and cysteine derivatives.

Authors:  Oleg A Levitskiy; Olga I Aglamazova; Yuri K Grishin; Tatiana V Magdesieva
Journal:  Beilstein J Org Chem       Date:  2022-09-08       Impact factor: 2.544

3.  Photoredox-catalyzed C-C bond cleavage of cyclopropanes for the formation of C(sp3)-heteroatom bonds.

Authors:  Liang Ge; Chi Zhang; Chengkai Pan; Ding-Xing Wang; Dong-Ying Liu; Zhi-Qiang Li; Pingkang Shen; Lifang Tian; Chao Feng
Journal:  Nat Commun       Date:  2022-10-08       Impact factor: 17.694
  3 in total

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