Silver‐Promoted Benzannulations of Siloxyalkynes with Pyridinium and Isoquinolinium Salts | Zendy

CabreraPardo Jaime R. | Zendy; Chai David I. | Zendy; Kozmin Sergey A. | Zendy

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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.

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