4.7 Article

Sulfoximines Assisted Rh(III)-Catalyzed C-H Activation/Annulation Cascade to Synthesize Highly Fused Indeno-1,2-benzothiazines

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 21, Pages 15217-15227

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01820

Keywords

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Funding

  1. National Natural Science Foundation of China [21632008, 21877118, 81620108027, 91953108]
  2. Science Technology Commission of Shanghai Municipality [18JC1411304, 18431907100]
  3. SASIBS Scholarship Program
  4. Youth Innovation Promotion Association CAS

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This study establishes a method for the synthesis of highly conjugated tetracyclic compounds through a Rh(III)-catalyzed reaction, characterized by high efficiency, broad substrate generality, and easy transformation.
A facile access to highly fused tetracyclic indeno-1,2-benzothiazines has been established via a Rh(III)-catalyzed C-H bond activation and intramolecular annulation cascade between sulfoximides and all-carbon diazo indandiones. This strategy is characterized by the fact that the diazo coupling partners do not require preactivation, along with its high efficiency, broad substrate generality, and facile transformation. Particularly, the highly conjugated tetracyclic products demonstrate good optical properties and can easily enter cells to emit bright fluorescence for live cell imaging.

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