Synthesis 2023; 55(05): 779-785
DOI: 10.1055/a-1953-4534
paper

Disilathiane as a Sulfur Source for the Construction of Isothiochromenes and Benzo[b]thiophenes by Copper-Catalyzed endo-Selective Hydrothiolation

Takumi Nakajima
,
Ryuki Takeuchi
,
Keita Oomori
,
Kento Ishida
,
Yohei Ogiwara
,
Norio Sakai
We thank the JSPS KAKENHI Grant Number (JP19K05463). Also, this research was partially supported by Ogawa Sho research fund.


Abstract

A copper-catalyzed construction of isothiochromenes and benzo[b]thiophenes via annulation with 1,1,1,3,3,3-hexamethyldisilathiane as a sulfur source is described. In the isothiochromene synthesis, the use of the disilathiane as a sulfur source successfully controls the regioselectivity of cyclization to afford the isothiochromene as the sole product. The present strategy can be applied to the synthesis of 2-aryl/2-alkylbenzo[b]thiophenes.

Supporting Information



Publication History

Received: 08 September 2022

Accepted: 29 September 2022

Accepted Manuscript online:
29 September 2022

Article published online:
09 November 2022

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