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Name Mr. Stephen Motika
Organization Chemistry Department at University of South Florida
Type Poster
Topic Organic Chemistry
Title

Recent advances in Homogenous Gold Catalysis: Constructing Carbon Heterocycles Containing Nitrogen-Boron Bonds

Author(s)

Stephen Motika; Xiaodong Shi

Author Location(s)

University of South Florida

Abstract

The combination of triazole/gold (TA-Au) and Cu(OTf)2 is identified as the optimal catalytic system for promoting intramolecular hydroboration for the synthesis of a six-membered cyclic amine–borane. Excellent yields (up to 95 %) and regioselectivities (5-exo vs. 6-endo) were achieved through catalyst control and sequential dilution. Good functional-group tolerance was attained, thus allowing the preparation of highly functionalized cyclic amine–borane substrates, which could not be achieved using other methods. Deuterium-labeling studies support the involvement of a hydride addition to a gold-activated alkyne with subsequent C−B bond formation