Journal
ORGANIC LETTERS
Volume 24, Issue 10, Pages 1924-1928Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c00294
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Funding
- JSPS KAKENHI [19K05466, 18H02014]
- JST CREST [JPMJCR20R1]
- Ritsumeikan Global Innovation Research Organization (R-GIRO) project
- Grants-in-Aid for Scientific Research [18H02014, 19K05466] Funding Source: KAKEN
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High reactivity of trimethoxyphenyl (TMP)-iodonium(III) acetate was achieved for phenol O-arylation. The cooperation of TMP ligand and acetate anion enhances the electrophilic reactivity towards phenol oxygen atoms. This ligand- and counterion-assisted strategy shows high applicability with tolerance towards various functional groups.
High reactivity of trimethoxyphenyl (TMP)-iodonium(III) acetate for phenol O-arylation was achieved. It was first determined that the TMP ligand and acetate anion cooperatively enhance the electrophilic reactivity toward phenol oxygen atoms. The proposed method provides access to various diaryl ethers in significantly higher yields than the previously reported techniques. Various functional groups, including aliphatic alcohol, boronic ester, and sterically hindered groups, were tolerated during O-arylation, verifying the applicability of this ligand- and counterion-assisted strategy.
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