4.8 Article

Exo-Selective Intramolecular C-H Alkylation with 1,1-Disubstituted Alkenes by Rare-Earth Catalysts: Construction of Indanes and Tetralins with an All-Carbon Quaternary Center

Journal

ACS CATALYSIS
Volume -, Issue -, Pages 12973-12983

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.2c0368112973ACS

Keywords

annulation; C-H activation; all-carbon quaternary center; scandium; yttrium; rare-earth-metal

Funding

  1. JSPS KAKENHI [JP22K05135]
  2. National Natural Science Foundation of China [22003001]
  3. Anhui Provincial Natural Science Foundation [2108085Y04]

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In this study, we report the exo-selective, regiospecific annulation of a wide range of functionalized aromatic substrates with 1,1-disubstituted alkenes through C(sp(2))-H and benzylic C(sp(3))-H activation using half-sandwich rare-earth catalysts. This protocol provides a straightforward and atom-efficient route for synthesizing indane and tetralin derivatives bearing an all-carbon quaternary stereocenter that were previously difficult to access using other catalysts. The reaction mechanism has been elucidated through deuterium-labeling experiments and DFT calculations.
We report herein the exo-selective, regiospecific annulation of a wide range of functionalized aromatic substrates with 1,1-disubstituted alkenes through C(sp(2))-H and benzylic C(sp(3))-H activation by half-sandwich rare-earth catalysts. This protocol offers a straightforward and atom-efficient route for the synthesis of a family of indane and tetralin derivatives bearing an all-carbon quaternary stereocenter that were difficult to access previously by other catalysts. The reaction mechanism has been elucidated by deuterium-labeling experiments and DFT calculations.

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