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Carbon Dioxide-Mediated C(sp2)–H Arylation of Primary and Secondary Benzylamines

preprint
revised on 30.11.2018 and posted on 30.11.2018 by Mohit Kapoor, Pratibha Chand-Thakuri, Michael Young
Carbon-carbon bond formation by transition metal-catalyzed C–H activation has become an important strategy to fabricate new bonds in a rapid fashion. Despite the pharmacological importance of ortho-arylbenzylamines, however, effective ortho-C–C bond formation from C–H bond activation of free primary and secondary benzylamines using PdII remains an outstanding challenge. Presented herein is a new strategy for constructing ortho-arylated primary and secondary benzylamines mediated by carbon dioxide (CO2). The use of CO2 is critical to allowing this transformation to proceed under milder conditions than previously reported, and that are necessary to furnish free amine products that can be directly used or elaborated without the need for deprotection. In cases where diarylation is possible, a chelate effect is demonstrated to facilitate selective monoarylation.

Funding

ACS Herman Frasch Foundation for Chemical Research 830-HF17

History

Email Address of Submitting Author

michael.young8@utoledo.edu

Institution

The University of Toledo

Country

United States of America

ORCID For Submitting Author

0000-0002-3256-5562

Declaration of Conflict of Interest

The authors have a provisional patent submitted related to this chemistry (United States Provisional Patent #62/608,074)

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in Journal of the American Chemical Society

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