SNAAP Sulfonimidate Alkylating Agent for Acids, Alcohols, and Phenols

Autor:	Nai-Chia Kuan, Christine N. Bradford, Joseph Kaladjian, Arturo Mejia, Alethea Poste, Haydi Elia, Michael Fimbres, Ali Abou-Zahr, Sylvia Kim, Andrea I-T. Chen, Jeremy Wood, Fan-Chun Meng, Tom J. Maricich, Therese Santos, Brett S. Kislin, Matthew J. Allan, Dianne Choi, Omonigho Aisagbonhi, Dustin Wride
Rok vydání:	2013
Předmět:	chemistry.chemical_classification Organic Chemistry Alkylation Catalysis Sulfonamide chemistry.chemical_compound chemistry Nucleophile Yield (chemistry) Organic chemistry Phenols Racemization Dichloromethane
Zdroj:	Synthesis. 45:3361-3368
ISSN:	1437-210X 0039-7881
Popis:	Stable, crystalline ethyl N-tert-butyl-4-nitrobenzenesulfonimidate has been prepared in high yield by direct O-ethylation of N-tert-butyl-4-nitrobenzenesulfonamide with iodoethane and silver(I) oxide in dichloromethane. This sulfonimidate directly ethylates various acids to esters; the stronger the acid, the faster it alkylates and in higher yield. It readily ethylates alcohols and phenols to ethers at room temperature in the presence of tetrafluoroboric acid catalyst without molecular rearrangements or racemization. We have defined these reactions as SNAAP alkylations: [substitution, nucleophilic of acids, alcohols and phenols]. The hard sulfonimidate alkylating agent is chemoselective, preferring oxygen > nitrogen > sulfur. The sulfonamide byproduct of alkylation is readily recycled to the sulfonimidate.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6b311d061ddfa919e2c6ed5fc8ed43bb https://doi.org/10.1055/s-0033-1339921 Zobrazit plný text záznamu