Issue 22, 2019

Regioselective synthesis of polycyclic sulfones via radical-induced three-component bicyclization cascades

Abstract

New radical-triggered three-component bicyclization cascades of 2-alkynyl aryldiazonium tetrafluoroborates with a sulfur dioxide surrogate DABCO·(SO2)2 and internal alkynes such as haloalkynes and ynones have been reported for the first time, leading to 49 examples of polycyclic sulfones with moderate to good yields and high levels of regioselectivity. This transformation initiated by an in situ generated arylsulfonyl radical proceeds efficiently under mild and neutral redox conditions, which provide an easy and metal-free pathway toward the formation of a range of richly decorated indeno[1,2-c]thiochromene 5,5-dioxides.

Graphical abstract: Regioselective synthesis of polycyclic sulfones via radical-induced three-component bicyclization cascades

Supplementary files

Article information

Article type
Communication
Submitted
14 jan 2019
Accepted
15 feb 2019
First published
15 feb 2019

Chem. Commun., 2019,55, 3227-3230

Regioselective synthesis of polycyclic sulfones via radical-induced three-component bicyclization cascades

X. Qin, L. He, J. Li, W. Hao, S. Tu and B. Jiang, Chem. Commun., 2019, 55, 3227 DOI: 10.1039/C9CC00324J

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