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Journal article
Interrupted S N Ar-Alkylation Dearomatization
JACS Au, v 4(3), pp 1118-1124
25 Mar 2024
PMID: 38559710
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
Dearomatizations provide powerful synthetic routes to rapidly assemble substituted carbocycles and heterocycles found in a plethora of bioactive molecules. Harnessing the advantages of dearomatization typically requires vigorous reagents because of the difficulty in disrupting the stable aromatic core. A relatively mild dearomatization strategy is described that employs lithiated nitriles or isocyanides in a simple S
Ar-type addition to form σ-complexes that are trapped by alkylation. The dearomatizations are diastereoselective and efficient and rapidly install two new carbon-carbon bonds, one of which is a quaternary center, as well as nitrile, isocyanide, and cyclohexadiene functionalities.
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Details
- Title
- Interrupted S N Ar-Alkylation Dearomatization
- Creators
- Bilal Altundas - University of Illinois at Urbana-ChampaignJohn-Paul R Marrazzo - Drexel University, Department of Chemistry, 3041 Chestnut Street, Philadelphia, Pennsylvania 19104, United StatesTore Brinck - KTH Royal Institute of TechnologyChristopher Absil - Temple UniversityFraser F Fleming - Drexel University, Department of Chemistry, 3041 Chestnut Street, Philadelphia, Pennsylvania 19104, United States
- Publication Details
- JACS Au, v 4(3), pp 1118-1124
- Publisher
- American Chemical Society
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:001166878900001
- Scopus ID
- 2-s2.0-85186098621
- Other Identifier
- 991021865115704721
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- Collaboration types
- Domestic collaboration
- International collaboration
- Web of Science research areas
- Chemistry, Multidisciplinary