Seminar
Tuesday, April 18, 2017 - 12:00am
Graduate student Caroline Bartulovich will be presenting
“Applications of Rh(III) in C-H Functionalization Reactions”
on April 18, 2017 at 4:10 PM in Neville Hall, Room 3.
Abstract
Despite its importance to many chemical processes, rhodium is one of the least abundant metals in the earth’s crust. The high cost of rhodium-containing products discourages its use in many applications despite having significant advantages over other transition metal catalysts. These benefits include low catalyst loadings, high functional group tolerance, and mild reaction conditions. In spite of its rarity, rhodium catalysis has yielded many useful transformations utilized by synthetic chemists that can be used in the synthesis of a variety of useful products such as bioactive molecules, agrochemicals, and natural products. Of its many possible oxidation states, Rh(III) is perhaps the most commonly encountered, and recently work has been done exploring the uses of Rh(III) in directed C-H bond functionalization reactions including alkylation of phenoxy moieties, alkylation with a,b-unsaturated carbonyl compounds, and cross-coupling reactions. Three recent examples of Rh(III) catalysis will be presented, all of which make use of (Cp*RhCl2)2 as the precatalytic species. The reaction examples that will be presented demonstrate the advantages of a rhodium catalytic system including low catalyst loadings, high functional group tolerance, and mild reaction conditions. Additionally, these examples were also chosen to demonstrate some of the challenges of Rh(III) catalyzed reactions as well. Overall, the work presented shows that further exploration of uses of rhodium in synthetic organic chemistry is warranted. References 1. Ravi, M.; Allu, S.; Swamy, K. C. K. The Journal of Organic Chemistry 2017, 82 (5), 2355–2363. 2. Zhang, Z.; Tang, M.; Han, S.; Ackermann, L.; Li, J. The Journal of Organic Chemistry 2017, 82 (1), 664–672. 3. Zhang, Y.; Zhao, H.; Zhang, M.; Su, W. Angewandte Chemie 2015, 127 (12), 3888–3892.“Applications of Rh(III) in C-H Functionalization Reactions”