Curiosity Driven New Reactivity Discovery

Friday, January 17, 2020

Dr. XiaoDong Michael Shi

Department of Chemistry

University of South Florida

Reception: Hand 1130 at 3:00 PM

Seminar: Hand 1144 at 3:30 PM

Abstract: Homogeneous gold catalysis has been developed explosively during the past decades. Despite the remarkable electrophilic activation of alkynes by cationic Au(I) catalysts, such as PPh3Au+, one challenge is to overcome their poor stability at high temperature. However, in order to activate some less reactive substrates, such as internal alkynes, harsher reaction conditions are usually required. As a good σ-donor and π-receptor, triazole has been applied as a ligand to improve the stability of cationic Au(I) catalysts. Taking advantage of the good stability of triazole-Au(I) complexes (TA-Au), we successfully achieved good reactivity of intermolecular hydroamination for both terminal and internal alkynes. Unlike previous reported gold catalysts, the TA-Au catalysts activate alkynes selectively over allenes. With this excellent chemoselectivity, TA-Au catalysts showed interesting reactivity in propargyl ester and vinyl ether rearrangement. This facilitates the development of otherwise challenging transformations, for instance, asymmetric synthesis of substituted allenes, Schmittel cyclization, dienal synthesis, and so on.

2017 - now: Professor, University of South Florida
2015- 2017: Associate Professor, University of South Florida
2005 - 2015: Assistant, Associate, Full Professor, West Virginia University
2002 - 2005: Postdoctoral Research Associate, University of California, Berkeley
1998 - 2002: Ph.D. University of Maryland
1994 - 1997: M.S. Nankai University
1990 - 1994: B.S., Nankai University

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