Synlett 2023; 34(19): 2319-2322
DOI: 10.1055/s-0042-1751490
letter

Pd-Catalyzed Intramolecular Cyclization–Thiocarbonylation Cascade Using Thioesters

Ryunosuke Ito
,
Yoshifumi Okura
,
Masahisa Nakada
This work was financially supported in part by the Japan Society for the Promotion of Science (JSPS KAKENHI Grant Numbers JP19H02725 and JP22H02087) and a Waseda University Grant for Special Research Projects.


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Abstract

A Pd-catalyzed intramolecular cyclization–thiocarbonylation cascade using thioesters is described. The developed cascade reaction afforded chromane, coumaran, indoline, and oxindole derivatives with a chiral quaternary carbon atom at the benzylic position in high to excellent yields. Relative to those observed in the previously reported relevant cascade using TIPSSPh, the yields with thioesters are almost the same or higher, depending on the substrate. Moreover, the use of thioesters significantly reduces the reaction time to less than one hour. Therefore, AcSPh is advantageous over TIPSSPh in terms of reaction time, atom economy, and cost effectiveness.

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Publication History

Received: 15 July 2023

Accepted after revision: 14 August 2023

Article published online:
18 September 2023

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