Impact of Adding -hexylamine to Nickel Metallophotoredox C-N Coupling to Form Diarylamines.

J Org Chem

School of Chemistry, State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, Dalian Key Laboratory of Intelligent Chemistry, Dalian University of Technology, Dalian 116024, China.

Published: January 2025

The mechanistic understanding of how alkylamines impact Ni-metallophotoredox C-N coupling to form diarylamines remains unclear. In this study, 12-alkylamines were evaluated as additives to determine their effects on the synthesis of diarylamines in a flow photochemical system. Notably, -hexylamine demonstrated the most significant promotional effect. Spectroscopic studies and experimental data reveal -hexylamine substitutes DABCO as a Ni catalyst ligand, enhancing yields particularly in sterically hindered arylamines.

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http://dx.doi.org/10.1021/acs.joc.4c02106DOI Listing

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