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Zn-mediated decarboxylative carbagermatranation of aliphatic N-hydroxyphthalimide esters: evidence for an alkylzinc intermediate

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Abstract

Alkyl nucleophiles synthesized by decarboxylation of the corresponding N-hydroxyphthalimide esters (NHP esters) would inherit the complex structure of natural carboxylic acids and result in useful cross-coupling fragments. Herein, we report the synthesis of alkyl carbagermatranes via Zn-mediated decarboxylation of NHP esters without Ni catalysis or photocatalysis. Mechanistic studies indicate that an alkyl zinc intermediate was involved; however, the generation of alkyl zinc will be inhibited in the presence of Ni. Hence, this study provides valuable resolution to the perplexing problem about whether organozinc was involved in recently emerging catalytic systems of NHP ester–Zn. Meanwhile, alkyl zinc reagents from NHP esters are compatible with aryl/alkyl bromides and iodides; therefore the scope of carbagermatranation in this work precedes that of in situ-generated organozinc from alkyl halides.

Graphical abstract: Zn-mediated decarboxylative carbagermatranation of aliphatic N-hydroxyphthalimide esters: evidence for an alkylzinc intermediate

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Publication details

The article was received on 25 Aug 2019, accepted on 13 Nov 2019 and first published on 14 Nov 2019


Article type: Edge Article
DOI: 10.1039/C9SC04288A
Chem. Sci., 2020, Advance Article
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Zn-mediated decarboxylative carbagermatranation of aliphatic N-hydroxyphthalimide esters: evidence for an alkylzinc intermediate

    W. Jiang, S. Yang, M. Xu, X. Xie and B. Xiao, Chem. Sci., 2020, Advance Article , DOI: 10.1039/C9SC04288A

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