Water Mediated Rearrangement of Alkynyl Cyclohexadienones: Access to meta-Alkenylated Phenols

Autor:	Ritu Sharma, Indranil Halder, Akshay M. Nair, Chandra M. R. Volla
Rok vydání:	2021
Předmět:	010405 organic chemistry Organic Chemistry Late stage Substrate (chemistry) 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Phenols Physical and Theoretical Chemistry Vinyl cation
Zdroj:	Organic Letters. 23:1840-1845
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.1c00245
Popis:	We report an efficient water mediated, Bronsted acid-catalyzed rearrangement of alkynyl cyclohexadienones to access meta-olefinated phenols under metal-free conditions. The reaction displayed excellent substrate scope and yields in water. Synthetic utility of the protocol was highlighted by carrying out gram scale synthesis, further functionalizations, and late stage modification. Mechanistic studies highlighted the key role of water, as the reaction proceeds via a water addition-elimination sequence on to a vinyl cation intermediate.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::40937805f479c6c8baf2c09a7b80e333 https://doi.org/10.1021/acs.orglett.1c00245 Zobrazit plný text záznamu