CANCELLED: Chemistry Seminar Series: Dr. Mark StradiottoExport this event to calendar

Wednesday, October 16, 2013 — 2:30 PM EDT

Addressing unmet reactivity challenges in Buchwald-Hartwig amination via catalyst design

Dr. Mark Stradiotto
Department of Chemistry
Dalhousie University

Wednesday, October 16, 2013
2:30 p.m.
C2-361 (Reading Room)

Abstract: The palladium-catalyzed amination of aryl and heteroaryl halides and pseudohalides with NH-containing substrates (i.e. Buchwald-Hartwig amination, BHA) is an indispensible component of the synthetic chemist’s toolkit that has been widely employed in the synthesis of pharmaceuticals, natural products and materials. Despite significant advances in BHA catalysis, a number of significant challenges persist, including but not restricted to: the monoarylation of the simplest of nitrogen substrates (e.g. ammonia, hydrazine); the use of challenging electrophilic reaction partners (e.g. aryl mesylates); chemoselective arylations of biologically relevant diamine substrates (e.g. tryptamine); and the identification of a “universal” catalyst for BHA that can be applied broadly with a range of N-H containing substrates. Research efforts in the Stradiotto group are in part directed toward addressing such unmet reactivity challenges in BHA and related transformations, through the design and application of new and/or existing catalyst systems. Our recent progress in this regard, including the development of our now commercialized “DalPhos” family of phosphine ligands, will be described in this presentation.  
 
Stradiotto and co-workers, selected references: Angew. Chem. Int. Ed., 2013, 52, 7242-7246; Adv. Synth. Catal., 2013, 355, 981-987; Chem. Eur. J., 2013, 19, 2131-2141; Chem. Eur. J., 2012, 18, 9758-9769; Chem. Commun., 2012, 48, 7277-7279; Chem. Commun., 2011, 47, 6936-6938; J. Am. Chem. Soc., 2011, 133, 5194-5197; J. Am. Chem. Soc., 2010, 132, 18026-18029; Angew. Chem. Int. Ed., 2010, 49, 8686-8690; Angew. Chem. Int. Ed., 2010, 49, 4071-4074. 

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