Issue 7, 2023

Tandem C- and O-alkylative annulation of β-ketosulfones with 1,2-bisbromomethyl arenes: one-pot construction of sulfonyl indanes and dioxadibenzofused macrocycles

Abstract

Herein, a tandem synthetic route for constructing sulfonyl indanes and dioxadibenzofused macrocycles is described. This strategy involves a transition-metal-free, base-mediated tandem C- and O-alkylative annulation of β-ketosulfones with 1,2-bisbromomethyl arenes with moderate to excellent yields under open-vessel reaction conditions. In the overall reaction process, two carbon–carbon (C–C) and two carbon–oxygen (C–O) bonds are formed. Various base-promoted reaction conditions are screened for this one-pot easy-to-operate conversion.

Graphical abstract: Tandem C- and O-alkylative annulation of β-ketosulfones with 1,2-bisbromomethyl arenes: one-pot construction of sulfonyl indanes and dioxadibenzofused macrocycles

Supplementary files

Article information

Article type
Paper
Submitted
02 Dec 2022
Accepted
12 Jan 2023
First published
13 Jan 2023

Org. Biomol. Chem., 2023,21, 1487-1500

Tandem C- and O-alkylative annulation of β-ketosulfones with 1,2-bisbromomethyl arenes: one-pot construction of sulfonyl indanes and dioxadibenzofused macrocycles

N. Hsueh, K. Chen and M. Chang, Org. Biomol. Chem., 2023, 21, 1487 DOI: 10.1039/D2OB02199D

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