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Imide arylation with aryl(TMP)iodonium tosylates.

ABSTRACT: 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.

SUBMITTER: Basu S

PROVIDER: S-EPMC6009222 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Imide arylation with aryl(TMP)iodonium tosylates.

Basu Souradeep S Sandtorv Alexander H AH Stuart David R DR

Beilstein journal of organic chemistry 20180511

Herein, we describe the synthesis of <i>N</i>-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 <i>N</i>-aryl phthalimides are moderate to high and the coupling reaction is compatible with electron-deficient and sterically encumbered aryl groups. ...[more]

PMID: 29977376

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