Visible-light-induced photocatalytic intermolecular cyclization for synthesis of 2,2-diarylchromanes

The photocatalytic cyclization of salicylaldehydes with 1,1-diarylalkenes for the synthesis of 2,2-diarylchromanes has been developed. The catalytic amount of Ir photocatalyst proceeds the cyclization to give the various 2,2-disubtitued chromanes under irradiation with blue LEDs. The obtained 2,2-diarylchromanes exhibit noticeable free-radical-scavenging activities, which have been largely unexplored. Notably, the chromane can convert to 2,2-diaryl-2H-naphtho[1,2- b ]pyran bearing strong electron withdrawing groups, which are found in various photochromic materials. Thus, the present reaction constitutes a promising tool for the synthesis of functional materials and biologically active compounds. • Visible-light-induced photocatalytic intermolecular cyclization for synthesis of 2,2-diarylchromanes has been developed. • The catalytic amount of Ir photocatalyst proceeds the cyclization to give the various electron-deficient 2,2-disubtitued chromanes under irradiation with blue LEDs. • ·The 2,2-diarylchromanes exhibit noticeable free-radical-scavenging activities. • The chromane can convert to electron-deficient 2,2-diaryl-2 H -naphtho[1,2- b ]pyran, which are found in various photochromic materials.

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Publication Details

Journal
Tetrahedron Letters
Published
2026-03-09
DOI
https://doi.org/10.1016/j.tetlet.2026.156034
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

Visible-light-induced photocatalytic intermolecular cyclization for synthesis of 2,2-diarylchromanes

Hiroyoshi Takamura, Isao Kadota, Sakura Kodaki, Junta Minato et al.
Tetrahedron Letters
Radical Photochemical Reactions
article

Visible-light-induced photocatalytic intermolecular cyclization for synthesis of 2,2-diarylchromanes

Hiroyoshi Takamura, Isao Kadota, Sakura Kodaki, Junta Minato, Makiya Nishikawa, Kosuke Kusamori, Shoko Itakura, Momo Kondo, Kenta Tanaka
article en

Abstract

The photocatalytic cyclization of salicylaldehydes with 1,1-diarylalkenes for the synthesis of 2,2-diarylchromanes has been developed. The catalytic amount of Ir photocatalyst proceeds the cyclization to give the various 2,2-disubtitued chromanes under irradiation with blue LEDs. The obtained 2,2-diarylchromanes exhibit noticeable free-radical-scavenging activities, which have been largely unexplored. Notably, the chromane can convert to 2,2-diaryl-2H-naphtho[1,2- b ]pyran bearing strong electron withdrawing groups, which are found in various photochromic materials. Thus, the present reaction constitutes a promising tool for the synthesis of functional materials and biologically active compounds. • Visible-light-induced photocatalytic intermolecular cyclization for synthesis of 2,2-diarylchromanes has been developed. • The catalytic amount of Ir photocatalyst proceeds the cyclization to give the various electron-deficient 2,2-disubtitued chromanes under irradiation with blue LEDs. • ·The 2,2-diarylchromanes exhibit noticeable free-radical-scavenging activities. • The chromane can convert to electron-deficient 2,2-diaryl-2 H -naphtho[1,2- b ]pyran, which are found in various photochromic materials.

Tetrahedron LettersVol. 179
Tokyo University of Science (JP), Okayama University (JP)
Openalex Percentile: Top 28%
Radical Photochemical Reactions
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Visible-light-induced photocatalytic intermolecular cyclization for synthesis of 2,2-diarylchromanes — Hiroyoshi Takamura, Isao Kadota, et al. · Tetrahedron Letters (2026) | TGRS Research Map | TGRS