Photoinduced stereoselective hydroalkylation of terminal arylalkynes via C(sp3)-H functionalization

A novel photoinduced stereoselective hydroalkylation of terminal arylalkynes via C(sp3)-H functionalization was developed. [Display omitted] A photoinduced stereoselective hydroalkylation of terminal arylalkynes via C(sp3)-H activation was developed. This method employed an organic dye 2,4,5,6-tetra...

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Published inTetrahedron letters Vol. 115; pp. 154321 - 154324
Main Authors Liu, Fen, Zhang, Kun, Zhao, Xiao-Fei, Meng, Qing-Xin, Zhao, Tian-Sheng, Tian, Wan-Fa, He, Yong-Qin
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 31.01.2023
Elsevier
Subjects
C(sp3)-H functionalization
Chemistry
Chemistry, Organic
Electron catalysis
Hydroalkylation of alkynes
Photoinduced reaction
Physical Sciences
Science & Technology
Hydroalkylation of alkynes
Photoinduced reaction
C(sp3)-H functionalization
Electron catalysis
C(SP)-H BONDS
ELECTRON
ACTIVATION
ACIDS
ALKYNES
C-H BONDS
PHOTOREDOX CATALYSIS
RADICAL REACTIONS
ALKENYLATION
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Summary:A novel photoinduced stereoselective hydroalkylation of terminal arylalkynes via C(sp3)-H functionalization was developed. [Display omitted] A photoinduced stereoselective hydroalkylation of terminal arylalkynes via C(sp3)-H activation was developed. This method employed an organic dye 2,4,5,6-tetrakis(carbazol-9-yl)-1,3‑dicyanobenzene (4CzIPN) as photosensitizer and N-hydroxyphthalimide (NHPI) as the HAT catalyst, which totally inhibited the usage of transition metals and stoichimetrical oxidant or radical initiators (e.g. TBHP). The method also displayed good functional tolerance, allowing access to 1,2-disubstituted alkenes in (Z)-major stereo-selectivity. Primary mechanism studies suggested that the reaction proceed via an electron-catalyzed process.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2022.154321