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Department of

Chemistry and Biochemistry

Title

Tim Clark, PhD, and Research Students Publish Paper

Message

Assistant Professor Tim Clark and his research students had an article published in Organic Letters entitled “Iridium-Catalyzed, Substrate-Directed C–H Borylation Reactions of Benzylic Amines.” The article is co-authored by USD undergraduate student Marissa Ringgold and three undergraduate students from Professor Clark’s past institution, Western Washington University.

Abstract:

The iridium-catalyzed arene C–H borylation reaction of benzylic amines has been developed, which inverts the
typical steric-controlled product distribution to provide ortho-substituted boronate esters. Picolylamine was found to
be an ideal ligand to replace 4,4'-di-tert-butylbipyridine to induce the directing effect. Preliminary experiments are
consistent with a mechanism involving dissociation of one amine of the hemilabile diamine ligand.

ContactTim Clark | clarkt@sandiego.edu | (619) 260-7703