Silver Triflate Catalyzed Cyclopropyl Carbinol Rearrangement for Benzo[b]oxepine and 2H-Chromene Synthesis

Autor:	Wan Teng Teo, Benjamin James Ayers, Chung-Hang Duncan Leung, Dik‐Lung Ma, Philip Wai Hong Chan, Bo Ra Lee, Shaun Wei Yong Koh
Rok vydání:	2015
Předmět:	chemistry.chemical_compound chemistry Stereochemistry Organic Chemistry 2H-chromene Phenols Physical and Theoretical Chemistry Selectivity Trifluoromethanesulfonate Derivative (chemistry) Adduct Catalysis
Zdroj:	European Journal of Organic Chemistry. 2015:4447-4456
ISSN:	1434-193X
DOI:	10.1002/ejoc.201500374
Popis:	An efficient AgOTf-catalyzed (TfO = trifluoromethanesulfonate) cyclopropyl carbinol rearrangement for the synthesis of benzo[b]oxepines and 2H-chromenes is reported by starting from 2-[cyclopropyl(hydroxy)methyl]phenols. The reactions proved to be general in scope and furnished a range of the corresponding functionalized oxygen heterocycles. The formation of the benzo-fused six-membered adduct is proposed to result from the ring-contraction of the benzo[b]oxepine derivative. Control of the product selectivity is achievable by fine-tuning the reaction time. The catalytic synergy between the silver(I) cation and the triflate anion was essential for optimal product yields.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::0d79f2ba05bf66cace7e7e1e0c790b41 https://doi.org/10.1002/ejoc.201500374 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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