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Synlett 2022; 33(15): 1546-1550
DOI: 10.1055/a-1863-8862
letter

2-Iodoxybenzoic Acid–Dimethyl Sulfoxide (IBX-DMSO)-Promoted Oxidative Aromatization of Spiro[2.5]octa-4,7-dien-6-one

Tong Li
a   College of Chemistry, Zhengzhou University, No. 100 Science Avenue, Zhengzhou, 450001, P. R. of China
,
Chaoxing Cui
a   College of Chemistry, Zhengzhou University, No. 100 Science Avenue, Zhengzhou, 450001, P. R. of China
,
Yuxia Zhang
b   School of Mathematics, Zhengzhou University of Aeronautics, No. 15 Wenyuan West Road, Zhengzhou, 450046, P. R. of China
,
Xixi Song∗
a   College of Chemistry, Zhengzhou University, No. 100 Science Avenue, Zhengzhou, 450001, P. R. of China
,
Zechao Wang  ∗
c   Division of Molecular Catalysis and Synthesis, Henan Institute of Advanced Technology, Zhengzhou University, Zhengzhou 450001, P. R. of China
,
Junbiao Chang∗
a   College of Chemistry, Zhengzhou University, No. 100 Science Avenue, Zhengzhou, 450001, P. R. of China
› Author AffiliationsThis research was supported by the Key Scientific Research Project in Universities of Henan Province (19A150049).
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Abstract

A 2-iodoxybenzoic acid (IBX)–dimethyl sulfoxide (IBX-DMSO)-promoted oxidative aromatization of spiro[2.5]octa-4,7-dien-6-ones has been developed. A series of substrates with various substitutions were transformed into oxidative aromatization products in good to excellent yields. This oxidative aromatization features environmentally friendly reagents, high efficiency, a broad substrate scope, broad functional-group tolerance, and mild reaction conditions.

Key words

metal-free reaction - iodoxybenzoic acid - dimethyl sulfoxide - oxidation - aromatization - spirooctadienones

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1863-8862.
  • Supporting Information


Publication History

Received: 21 February 2022

Accepted after revision: 30 May 2022

Accepted Manuscript online:
30 May 2022

Article published online:
15 June 2022

© 2022. Thieme. All rights reserved

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