Functionalization of 2‐Aryl‐2 H ‐1,2,3‐Triazoles by Reaction of Triazole‐ N ‐Oxides With o ‐Silylaryl Triflates: A New Tale From Aryne Chemistry

The first study of the functionalization of 2‐aryl‐2 H ‐1,2,3‐triazole N ‐oxides via aryne chemistry is reported. Under optimized conditions using TBAF in DCM, various N ‐oxides react with arynes generated from o ‐silylaryl triflates to afford 2‐(2‐aryl‐2 H ‐1,2,3‐triazol‐4‐yl)phenols in moderate‐to‐excellent yields (41%–91%). Notably, N ‐oxides bearing a methoxycarbonyl group at the 4‐position undergo a subsequent intramolecular cyclization, yielding 2‐arylchromeno[3,4‐ d ][1,2,3]triazol‐4(2 H )‐ones. The latter compounds exhibit violet‐to‐blue photoluminescence with quantum yields of up to 72% in solution and up to 28% in solid state, depending on the substituent pattern. This work establishes a versatile and straightforward route to both triazolylphenols and fluorescent chromenotriazolones.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2026-10-28
DOI
https://doi.org/10.1002/ejoc.70947
Primary Topic
Cyclization and Aryne Chemistry
Type
article
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0.00

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article

Functionalization of 2‐Aryl‐2 H ‐1,2,3‐Triazoles by Reaction of Triazole‐ N ‐Oxides With o ‐Silylaryl Triflates: A New Tale From Aryne Chemistry

Valentina Kotlyarova, Vadim P. Boyarskiy, Kristina S. Kisel, Svetlana O. Baykova et al.
European Journal of Organic Chemistry
Cyclization and Aryne Chemistry
article

Functionalization of 2‐Aryl‐2 H ‐1,2,3‐Triazoles by Reaction of Triazole‐ N ‐Oxides With o ‐Silylaryl Triflates: A New Tale From Aryne Chemistry

Valentina Kotlyarova, Vadim P. Boyarskiy, Kristina S. Kisel, Svetlana O. Baykova, Artem V. Semenov, Sergey V. Baykov, Шетнев Антон Андреевич, Valeria A. Panova, Leonid L. Fershtat, Evgeny Kh. Sadykov, Marina S. Vasileva
article en

Abstract

The first study of the functionalization of 2‐aryl‐2 H ‐1,2,3‐triazole N ‐oxides via aryne chemistry is reported. Under optimized conditions using TBAF in DCM, various N ‐oxides react with arynes generated from o ‐silylaryl triflates to afford 2‐(2‐aryl‐2 H ‐1,2,3‐triazol‐4‐yl)phenols in moderate‐to‐excellent yields (41%–91%). Notably, N ‐oxides bearing a methoxycarbonyl group at the 4‐position undergo a subsequent intramolecular cyclization, yielding 2‐arylchromeno[3,4‐ d ][1,2,3]triazol‐4(2 H )‐ones. The latter compounds exhibit violet‐to‐blue photoluminescence with quantum yields of up to 72% in solution and up to 28% in solid state, depending on the substituent pattern. This work establishes a versatile and straightforward route to both triazolylphenols and fluorescent chromenotriazolones.

European Journal of Organic Chemistry
Russian Academy of Sciences (RU), St Petersburg University (RU), N.D. Zelinsky Institute of Organic Chemistry (RU), Novosibirsk Institute of Organic Chemistry (RU), Yaroslavl State Pedagogical University (RU)
Saint Petersburg State University, Russian Science Foundation, Division of Materials Research
Openalex Percentile: Top 26%
Cyclization and Aryne Chemistry
DOIOpen Access PDFOpenAlex
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