Journal
ACS CATALYSIS
Volume 12, Issue 20, Pages 12973-12983Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.2c03681
Keywords
annulation; C; H activation; all-carbon quaternary center; scandium; yttrium; rare-earth-metal
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Funding
- JSPS KAKENHI [JP22K05135]
- National Natural Science Foundation of China [22003001]
- Anhui Provincial Natural Science Foundation [2108085Y04]
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This study reports the exo-selective, regiospecific annulation of a wide range of functionalized aromatic substrates with 1,1-disubstituted alkenes through C(sp2)-H and benzylic C(sp3)-H activation by half-sandwich rare-earth catalysts. It provides a straightforward and atom-efficient method for the synthesis of indane and tetralin derivatives bearing an all-carbon quaternary stereocenter that were previously difficult to access by other catalysts. The reaction mechanism has been elucidated using 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(sp2)-H and benzylic C(sp3)-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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