Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 21, Pages 13895-13905Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01917
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Funding
- National Science Foundation [Che-1664565, Che-1955086]
- SDSU Graduate Student Fellowship
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We report a highly efficient ortho-selective electrophilic chlorination of phenols utilizing a Lewis basic selenoether catalyst. The selenoether catalyst resulted in comparable selectivities to our previously reported bis-thiourea ortho-selective catalyst, with a catalyst loading as low as 1%. The new catalytic system also allowed us to extend this chemistry to obtain excellent ortho-selectivities for unprotected anilines. The selectivities of this reaction are up to >20:1 ortho/para, while the innate selectivities for phenols and anilines are approximately 1:4 ortho/para. A series of preliminary studies revealed that the substrates require a hydrogen-bonding moiety for selectivity.
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