Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 14, Issue -, Pages 1034-1038Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.14.90
Keywords
arylation; C-N coupling; diaryliodonium; hypercoordinate iodine; metal-free
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Funding
- Portland State University
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Herein, we describe the synthesis of N-aryl phthalimides by metal-free coupling of potassium phthalimide with unsymmetrical aryl(TMP) iodonium tosylate salts. The aryl transfer from the iodonium moiety occurs under electronic control with the electron-rich trimethoxyphenyl group acting as a competent dummy ligand. The yields of N-aryl phthalimides are moderate to high and the coupling reaction is compatible with electron-deficient and sterically encumbered aryl groups.
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