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Silver‐Promoted Benzannulations of Siloxyalkynes with Pyridinium and Isoquinolinium Salts
Author(s) -
CabreraPardo Jaime R.,
Chai David I.,
Kozmin Sergey A.
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300443
Subject(s) - pyridinium , chemistry , adduct , bicyclic molecule , stoichiometry , fragmentation (computing) , organic chemistry , computer science , operating system
We describe the development of efficient benzannulations of siloxyalkynes with pyridinium and isoquinolinium salts. Such reactions are successfully promoted by a stoichiometric amount of silver(I) benzolate under mild reaction conditions. This process proceeds via a formal inverse‐electron demand Diels–Alder reaction, followed by fragmentation of the initially produced bicyclic adducts to deliver a range of synthetically useful phenols and naphthols.