Rh-Catalyzed Reactions of 1,4-Benzoquinones with Electrophiles: C-H Iodination, Bromination, and Phenylselenation

Guilherme A M Jardim, John F. Bower*, Eufrânio N. Da Silva Júnior

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

31 Citations (Scopus)
315 Downloads (Pure)

Abstract

Under Rh-catalyzed conditions, typically electrophilic 1,4-benzoquinones exhibit nucleophilic reactivity, such that exposure to appropriate electrophiles generates products of C-H iodination, bromination, and phenylselenation. This provides a mild and general method for direct halofunctionalization, and the first method that can achieve direct C-H phenylselenation of this compound class. The scope and limitations of the new protocols are outlined, and representative derivatizations are highlighted.

Original languageEnglish
Pages (from-to)4454-4457
Number of pages4
JournalOrganic Letters
Volume18
Issue number18
Early online date7 Sep 2016
DOIs
Publication statusPublished - 16 Sep 2016

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