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Connecting Remote C–H Bond Functionalization and Decarboxylative Coupling Using Simple Amines

preprint
submitted on 17.09.2019, 14:37 and posted on 24.09.2019, 16:32 by Francisco de Azambuja, Ming-Hsiu Yang, Alexander Bruecker, Paul Cheong, Ryan Altman
The manuscript describes a Pd-catalyzed reaction of benzylic electrophiles that gives para-substituted arene products. Mechanistic studies suggest a mechanism involving a dearomative C–C bond-forming step, followed by base-mediated rearomatization. This mechanism is uncommon and underappreciated in Pd-catalysis and further exploitation of this mechanism should enable access to other organic molecules.

Funding

Herman Frasch Foundation for Chemical Research (701- HF12)

National Science Foundation (CHE-1455163)

NIH Shared Instrumentation Grants S10OD016360 and S10RR024664

NSF Major Research Instrumentation Grants 9977422 and 0320648

NIH Center Grant P20GM103418

National Science Foundation (NSF, CHE-1352663)

NSF Center for Sustainable Materials Chemistry (NSF CHE-1102637)

History

Email Address of Submitting Author

raaltman@ku.edu

Institution

The University of Kansas

Country

United States

ORCID For Submitting Author

0000-0002-8724-1098

Declaration of Conflict of Interest

No conflicts of interest are reported

Version Notes

Initial submission prior to peer review

Exports