Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 44, Pages 14658-14667Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b07981
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Funding
- NSF-CAREER Award [1254397]
- Wisconsin Alumni Research Foundation
- NSF [CHE-9208463, CHE-9629688, BIR-0214394]
- NIH [RR08389-01, P41GM103399, S10RR08438, S10RR029220]
- National Science Foundation [CHE01205646, CHE-0840494]
- UW-Madison Center For High Throughput Computing (CHTC) in the Department of Computer Sciences
- UW-Madison
- Advanced Computing Initiative
- Wisconsin Institutes for Discovery
- National Science Foundation
- U.S. Department of Energy's Office of Science
- NIGMS [P41-GM103311]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1254397] Funding Source: National Science Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1205646] Funding Source: National Science Foundation
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The development of new catalysts for selective nitrene transfer is a continuing area of interest. In particular, the ability to control the chemoselectivity of intermolecular reactions in the presence of multiple reactive sites has been a long-standing challenge in the field. In this paper, we demonstrate examples of silver-catalyzed, nondirected, intermolecular nitrene transfer reactions that are both chemoselective and flexible for aziridination or C-H insertion, depending on the choice of ligand. Experimental probes present a puzzling picture of the mechanistic details of the pathways mediated by [((t)Bu(3)tpy)AgOTf](2) and (tpa)AgOTf. Computational studies elucidate these subtleties and provide guidance for the future development of new catalysts exhibiting improved tunability in group transfer reactions.
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