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Issue 26, 2018
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Unusual biaryl torsional strain promotes reactivity in Cu-catalyzed Sommelet–Hauser rearrangement

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Abstract

A Cu-catalyzed Sommelet–Hauser dearomatization of dihydrophenanthridine and diazo compounds is reported for the synthesis of spiro-indolines. A spiro-structure with adjacent quaternary and tertiary carbon centers was constructed in one step as a single isomer. Increasing steric hindrance by introducing ortho-substituents dramatically improved substrate reactivity in this transformation.

Graphical abstract: Unusual biaryl torsional strain promotes reactivity in Cu-catalyzed Sommelet–Hauser rearrangement

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Publication details

The article was received on 11 Apr 2018, accepted on 13 Jun 2018 and first published on 14 Jun 2018


Article type: Edge Article
DOI: 10.1039/C8SC01657G
Citation: Chem. Sci., 2018,9, 5850-5854
  • Open access: Creative Commons BY-NC license
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    Unusual biaryl torsional strain promotes reactivity in Cu-catalyzed Sommelet–Hauser rearrangement

    C. Pan, W. Guo and Z. Gu, Chem. Sci., 2018, 9, 5850
    DOI: 10.1039/C8SC01657G

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