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SUMMARY:Independent Research Proposal
LOCATION:Chemistry A101
TZID:America/Denver
DTSTART:20240523T160000
UID:2026-04-24-07-33-32@natsci.colostate.edu
DTSTAMP:20260424T073332
Description:Six-membered aromatic rings are ubiquitous in natural products\
 , drugs\, and agrochemicals. Classical approaches to functionalize arenes 
 involve electrophilic aromatic substitution (EAS) and nucleophilic aromati
 c substitution (SNAr) reactions to install a single substituent directly o
 n the carbon framework. However\, pre-installed functional groups and elec
 tron-withdrawing substituents are required for successful functionalizatio
 n with nucleophiles. In addition\, EAS reactions are guided by pre-existin
 g substituents on the arene ring. Electron-rich substituents guide these e
 lectrophilic processes to the ortho and para positions. Thus\, a synthetic
  challenge arises for meta-selective nucleophilic functionalization of ele
 ctron-rich arenes. I present an alternative method to achieve meta-selecti
 ve functionalization directly from the C-H bond using a benzene dearomatiz
 ation strategy mediated by row 6 transition metal complexes. Diels-Alder r
 eactions from the dearomatized intermediate with alkynes will allow direct
  di-functionalization at the ortho and meta positions of these arenes. In 
 addition\, using nitriles\, tetrahydropyridines\, isocyanates\, aryldiazon
 ium salts\, and imines as dienophiles in hetero-Diels-Alder reactions allo
 ws for transmutation of the benzene core into a variety of N-heterocycles.
     4:00 pm
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