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Issue 90, 2019

ZnI2/Zn(OTf)2-TsOH: a versatile combined-acid system for catalytic intramolecular hydrofunctionalization and polyene cyclization

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Abstract

A mild and efficient combined-acid system using a zinc(II) salt [ZnI2 or Zn(OTf)2] and p-toluene sulfonic acid (TsOH) was investigated for catalytic cationic cyclizations, including intramolecular hydrocarboxylation, hydroalkoxylation, hydroamination, hydroamidation, hydroarylation and polyene cyclizations. This reaction provides easy access to five- and six-membered O- and N-containing saturated heterocyclic compounds, tetrahydronaphthalene derivatives and polycyclic skeletons in excellent yield with perfect Markovnikov selectivity and under mild conditions. The operational simplicity, broad applicability, and use of inexpensive commercially available catalysts make this protocol superior to existing methodologies.

Graphical abstract: ZnI2/Zn(OTf)2-TsOH: a versatile combined-acid system for catalytic intramolecular hydrofunctionalization and polyene cyclization

Supplementary files

Article information


Submitted
16 Sep 2019
Accepted
17 Oct 2019
First published
17 Oct 2019

Chem. Commun., 2019,55, 13522-13525
Article type
Communication

ZnI2/Zn(OTf)2-TsOH: a versatile combined-acid system for catalytic intramolecular hydrofunctionalization and polyene cyclization

T. Chou, B. Yu and R. Chein, Chem. Commun., 2019, 55, 13522 DOI: 10.1039/C9CC07242J

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