Files and links (1)
Published, Version of Record (VoR)Open Access (License Unspecified), Open
Journal article
Dearomatization of aromatic asmic isocyanides to complex cyclohexadienes
Nature communications, v 13(1), pp 6444-6444
28 Oct 2022
PMID: 36307409
Abstract
A dearomatization-dislocation-coupling cascade rapidly transforms aromatic isocyanides into highly functionalized cyclohexadienes. The facile cascade installs an exceptional degree of molecular complexity: three carbon-carbon bonds, two quaternary stereocenters, and three orthogonal functionalities, a cyclohexadiene, a nitrile, and an isocyanide. The tolerance of arylisocyanides makes the method among the mildest dearomatizations ever reported, typically occurring within minutes at -78 °C. Experimental and computational analyses implicate an electron transfer-initiated mechanism involving an unprecedented isocyanide rearrangement followed by radical-radical anion coupling. The dearomatization is fast, proceeds via a complex cascade mechanism supported by experimental and computational insight, and provides complex, synthetically valuable cyclohexadienes.
Metrics
Details
- Title
- Dearomatization of aromatic asmic isocyanides to complex cyclohexadienes
- Creators
- Bilal Altundas - Drexel UniversityEmbarek Alwedi - MSDZhihui Song - Department of Chemistry and Biochemistry, University of Maryland, 8051 Reagents Drive, College Park, MD, 20742, USAAchyut Ranjan Gogoi - Texas A&M UniversityRyan Dykstra - University of Maryland, College ParkOsvaldo Gutierrez - Texas A&M UniversityFraser F Fleming - Drexel University, Chemistry
- Publication Details
- Nature communications, v 13(1), pp 6444-6444
- Publisher
- Springer Nature
- Grant note
- R35 GM137797 / NIGMS NIH HHS
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000886265500019
- Scopus ID
- 2-s2.0-85140846859
- Other Identifier
- 991021899413804721
InCites Highlights
Data related to this publication, from InCites Benchmarking & Analytics tool:
- Collaboration types
- Industry collaboration
- Domestic collaboration
- Web of Science research areas
- Chemistry, Multidisciplinary