Issue 16, 2019

Facile synthesis of biarylmethanes and tetrasubstituted arenes via a base-mediated [3 + 3] benzannulation reaction of Morita–Baylis–Hillman adducts and unsaturated sulfones

Abstract

A facile DBU-mediated [3 + 3] benzannulation reaction of 1,3-bis-sulfonyl propenes and Morita–Baylis–Hillman (MBH) bromides is described. The benzannulation reaction afforded bis-sulfonyl biarylmethanes/arenes with complete regioselectivity. The products may be converted readily into corresponding benzophenones via site-selective benzylic oxidation.

Graphical abstract: Facile synthesis of biarylmethanes and tetrasubstituted arenes via a base-mediated [3 + 3] benzannulation reaction of Morita–Baylis–Hillman adducts and unsaturated sulfones

Supplementary files

Article information

Article type
Paper
Submitted
26 Jan 2019
Accepted
01 Apr 2019
First published
01 Apr 2019

Org. Biomol. Chem., 2019,17, 4073-4076

Facile synthesis of biarylmethanes and tetrasubstituted arenes via a base-mediated [3 + 3] benzannulation reaction of Morita–Baylis–Hillman adducts and unsaturated sulfones

D. Yadav, S. K. Sharma and R. S. Menon, Org. Biomol. Chem., 2019, 17, 4073 DOI: 10.1039/C9OB00214F

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