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Silver-Promoted Benzannulations of Siloxy Alkynes with Pyridinium and Isoquinolinium Salts.

ABSTRACT: We describe the development of efficient benzannulations of siloxy alkynes 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.

SUBMITTER: Cabrera-Pardo JR

PROVIDER: S-EPMC3956059 | biostudies-literature | 2013 Sep

REPOSITORIES: biostudies-literature

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Silver-Promoted Benzannulations of Siloxy Alkynes with Pyridinium and Isoquinolinium Salts.

Cabrera-Pardo Jaime R JR Chai David I DI Kozmin Sergey A SA

Advanced synthesis & catalysis 20130901 13

We describe the development of efficient benzannulations of siloxy alkynes 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. ...[more]

PMID: 24653670

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