Synthesis of highly fluorescent helical quinolizinium salts by a Rh-catalyzed cyclotrimerization/C-H activation sequence.

IF 4.3 2区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Chemical Communications Pub Date : 2025-02-05 DOI:10.1039/d4cc06512c
Timothée Cadart, Lucia Feriancová, Petr Henke, Robert Gyepes, Ivana Císařová, Květa Kalíková, Martin Kotora
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引用次数: 0

Abstract

A series of helical quinolizinium salts were prepared utilizing Rh-catalyzed [2+2+2]cyclotrimerization and C-H activation processes as the crucial synthetic steps. The cyclotrimerization of appropriately substituted diynes with trimethylsilylethyne under Rh-catalyzed conditions provided the 1-arylisoquinolines in up to 61% isolated yields. Their Rh-catalyzed C-H activation/annulation with various aryl and alkyl disubstituted alkynes gave rise to [7]-helical quinolizinium salts in high isolated yields (up to 93%). Enantioselective C-H activation was also tried with asymmetric induction up to 62% ee. The respective boron and platinum complexes of 1-arylisoquinolines were prepared as well. All prepared compounds exhibit fluorescence in the orange-red light region (606-682 nm) with ΦFs 28-99%.

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来源期刊
Chemical Communications
Chemical Communications 化学-化学综合
CiteScore
8.60
自引率
4.10%
发文量
2705
审稿时长
1.4 months
期刊介绍: ChemComm (Chemical Communications) is renowned as the fastest publisher of articles providing information on new avenues of research, drawn from all the world''s major areas of chemical research.
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