University of Calgary
Detian (Tim) Gao, PhD Candidate.
Submitted by jcrawfo on Tue, 2011-11-22 16:59.
2011-12-12 03:59
2011-12-12 15:59
DEPARTMENT OF CHEMISTRY
CHEMISTRY 601/603
FINAL PhD PRESENTATION
SPEAKER: Detian (Tim) Gao, PhD Candidate.
DATE: Monday, Dec. 12, 2011
TIME: 3:00 pm
PLACE: ST 143
TITLE: “Synthesis of Indoles via Copper-Catalyzed Cyclizations of o-Haloaryl Enamines”
ABSTRACT:
Indole is an important nitrogen heterocycle and it is prevalent in many biologically active compounds. This presentation will tell the story of how we developed a novel and versatile method for the synthesis of multisubstituted indoles via an intramolecular ligand-free copper-catalyzed C-arylation of sulfonyl enamines from a less successful palladium-catalyzed approach. The presentation also includes our attempt to explain the regioselectivity, the site selectivity, the true active catalyst, the dual roles of both the substrates and solvent of this cyclization, as well as the expansion of this method to enaminone and enaminoate substrates. The application of this method to solid phase indole synthesis and the synthesis of two medicinal compounds will also be described.
Graduate Program
