Transient Directing Group enabled C3-(sp2)-H alkenylation of Five Membered Heterocyclic Aldehydes: An Easy Access to Mechanochromic Luminogens

18 May 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The palladium (II) catalyzed direct C3-(sp2)-H alkenylation of five membered heterocyclic aldehydes has been developed using 3-aminobutanoic acid as a catalytic transient directing group. A wide range of heterocyclic aldehydes reacted with various acrylates to afford highly site-selective C3 alkenylated products. This method features an exclusive E-selective alkenylation at the C3-position of heterocyclic aldehydes with a broad substrate scope in good to excellent yields. The protocol also gave direct access to few novel compounds that are proved to be mechanochromic luminsescent materials.

Keywords

palladium
C-H activation
alkenylation
heterocyclic aldehydes
mechanochromism

Supplementary materials

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Title
Transient Directing Group enabled C3-(sp2)-H alkenylation of Five Membered Heterocyclic Aldehydes: An Easy Access to Mechanochromic Luminogens
Description
The Supporting information includes general experimental procedures and details, spectroscopic data, Copies of spectra and single crystal X-ray data.
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