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

Nai-Chen Hsueh; Kuan-Ting Chen; Meng-Yang Chang

doi:10.1039/d2ob02199d

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

Org Biomol Chem. 2023 Feb 15;21(7):1487-1500. doi: 10.1039/d2ob02199d.

Authors

Nai-Chen Hsueh¹, Kuan-Ting Chen¹, Meng-Yang Chang^{1

2

3}

Affiliations

¹ Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan. mychang@kmu.edu.tw.
² Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan.
³ NPUST College of Professional Studies, National Pingtung University of Science and Technology, Pingtung 912, Taiwan.

PMID: 36661132
DOI: 10.1039/d2ob02199d

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.