Radical Anion Promoted Chemoselective Cleavage of Csp2–S Bond Enables Formal Cross-Coupling of Aryl Methyl Sulfones with Alcohols

Autor:	Tianxin Wang, Jixiang Bai, Tiezheng Jia, Qingchao Liu, Botao Dai, Peiyuan Yu
Rok vydání:	2021
Předmět:	chemistry.chemical_classification Nucleophilic addition Radical-nucleophilic aromatic substitution Aryl radical Chemistry Aryl Organic Chemistry Cleavage (embryo) Biochemistry Medicinal chemistry chemistry.chemical_compound Alkoxide Physical and Theoretical Chemistry Chemoselectivity Alkyl
Zdroj:	Organic Letters. 23:5761-5765
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.1c01926
Popis:	A novel formal cross-coupling of aryl methyl sulfones and alcohols affording alkyl aryl ethers via an SRN1 pathway is developed. Two marketed antitubercular drugs were efficiently prepared employing this approach as the key step. A dimsyl-anion initiated radical chain process was revealed as the major pathway. DFT calculations indicate that the formation of a radical anion via nucleophilic addition of alkoxide to the aryl radical is the key step in determining the observed chemoselectivity.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b5c31085462a6cfc0a2c93db3c57d5d8 https://doi.org/10.1021/acs.orglett.1c01926 Zobrazit plný text záznamu