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A Rapid Entry into Thioflavanones via Conjugate Additions of Diarylcuprates to Thiochromones

Undergraduate #186
Discipline: Chemistry and Chemical Sciences
Subcategory: Chemistry (not Biochemistry)

Briana Graves - Winston-Salem State University
Co-Author(s): Malcolm Jeffries and Shekinah Graham, Winston-Salem State University, Winston-Salem, NC



Thiochromone undergo conjugate addition reactions with arylcuprates to afford 2-substituted thio- flavanones, providing an efficient synthetic approach to privileged sulfur-containing structural motifs and valuable precursor for many pharmaceuticals. Excellent yields of substituted thioflavanones are achieved with lithium diarylcuprates, lithium arylcyanocuprates and Grignard reagents with copper catalysis. This method provides a rapid entry to a variety of thioflavanones in excellent yields (up to 92%). The use of commercially available or easily prepared organometallic reagents will expedite the synthesis of a large library of thioflavanones for further synthetic applications and biological studies.

Not Submitted

Funder Acknowledgement(s): This is funded by, National science foundation HBCU-UP RIA award to Dr. Guo. Award number 1600987.

Faculty Advisor: Fenghai Guo, guof@wssu.edu

Role: In this research, I conducted conjugate addition reactions to arylcuprates to thiochromone. This is the first example of organocuprates addition to thiochromone. This apporach provides a rapid entry into privileged sulfur-containing structural motifs and valuable precursor for many pharmaceuticals.

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This material is based upon work supported by the National Science Foundation (NSF) under Grant No. DUE-1930047. Any opinions, findings, interpretations, conclusions or recommendations expressed in this material are those of its authors and do not represent the views of the AAAS Board of Directors, the Council of AAAS, AAAS’ membership or the National Science Foundation.

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