Presentation Title

Regioselective Ring Closing of Aromatic Alkynes and the Influence of Gold Cavitands

Faculty Mentor

Michael P. Schramm

Start Date

17-11-2018 12:30 PM

End Date

17-11-2018 2:30 PM

Location

CREVELING 94

Session

POSTER 2

Type of Presentation

Poster

Subject Area

physical_mathematical_sciences

Abstract

Regioselective Ring Closing of Aromatic Alkynes and the Influence of Gold Cavitands

Lisa E. Rusali, Michael P. Schramm, Ph.D

Department of Chemistry and Biochemistry, California State University, Long Beach, Long Beach, CA 90840

Gold cavitands have some features resembling enzymes and can therefore facilitate catalysis. They have been of great interest in our lab as we investigate their applications in molecular transformations. The experiments we have designed test the cavitand’s functionality, focusing on ring closing reactions with aromatic terminal alkynes. We can test special features of our gold cavitands by comparing them directly to the simple salt AuCl. We hypothesize that the substrate can both enter and cyclize intramolecularly using the terminal alkyne functional group. Furthermore, upon influence of the cavitand, the substrate can either close into a 5-membered or 6-membered ring. We also anticipate the cavitand can cyclize substrates that otherwise would not transform using AuCl alone. To date, 5 analogs of the substrate have been synthesized and tested using the gold cavitands. We have found the cavitand favors 6-membered rings for a majority of the substrates and cyclization occurs faster and more cleanly than with the simple AuCl salt. The results of these experiments can provide a gold mine of information, with further understanding of the capabilities and limitations of the cavitands as they are applied to catalysis.

This project is supported by RISE (LER) (NIH 2R25GM071638-09A1), NSF (MPS) (RUI CHE-1708937) 6/1/2017 - 5/31/2020, NMR instruments on NSF (MPS) (MRI CHE-1337559)

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Nov 17th, 12:30 PM Nov 17th, 2:30 PM

Regioselective Ring Closing of Aromatic Alkynes and the Influence of Gold Cavitands

CREVELING 94

Regioselective Ring Closing of Aromatic Alkynes and the Influence of Gold Cavitands

Lisa E. Rusali, Michael P. Schramm, Ph.D

Department of Chemistry and Biochemistry, California State University, Long Beach, Long Beach, CA 90840

Gold cavitands have some features resembling enzymes and can therefore facilitate catalysis. They have been of great interest in our lab as we investigate their applications in molecular transformations. The experiments we have designed test the cavitand’s functionality, focusing on ring closing reactions with aromatic terminal alkynes. We can test special features of our gold cavitands by comparing them directly to the simple salt AuCl. We hypothesize that the substrate can both enter and cyclize intramolecularly using the terminal alkyne functional group. Furthermore, upon influence of the cavitand, the substrate can either close into a 5-membered or 6-membered ring. We also anticipate the cavitand can cyclize substrates that otherwise would not transform using AuCl alone. To date, 5 analogs of the substrate have been synthesized and tested using the gold cavitands. We have found the cavitand favors 6-membered rings for a majority of the substrates and cyclization occurs faster and more cleanly than with the simple AuCl salt. The results of these experiments can provide a gold mine of information, with further understanding of the capabilities and limitations of the cavitands as they are applied to catalysis.

This project is supported by RISE (LER) (NIH 2R25GM071638-09A1), NSF (MPS) (RUI CHE-1708937) 6/1/2017 - 5/31/2020, NMR instruments on NSF (MPS) (MRI CHE-1337559)