We
herein report the first visible-light-mediated cross-coupling
of unactivated alkyl iodides with aryl bromides through synergistic
halogen atom transfer (XAT) and nickel catalysis. This simple protocol
operates under mild reaction conditions and tolerates a variety of
functional groups affording C(sp
3)–C(sp
2) cross-coupling products in good to moderate
yields.
In the early days of synthetic organic chemistry Hantzsch esters (HEs) were bio-inspired hydride donors and often used for the reduction of C=X (X=C, N, O) bonds. Recently, it has been proved that HEs and their derivatives (4-Alkyl-or acyl-Hantzsch esters) serve as electron donor, proton source, hydrogen atom donor, alkyl and acyl radical precursors in photoredox catalysis. Recently it was found that the excited-state of HEs has also been identified as a strong photo reductant in the absence of photocatalyst and also, the donor of HE forms EDA-complexes with organic molecules and triggers SET process to generate carbon radical entities. This minireview focuses on the recent chemistry developments where Hantzsch esters act as a photo reductant in organic synthesis, with a special focus on the reaction mechanisms. We hope that this review will help in the further development of radical-based organic transformations in absence of external photocatalysts.
An efficient, catalyst- and additive-free, visible-light-driven
radical C3–H alkylation of quinoxalin-2(1H)-one derivatives has been developed. This reaction utilizes alkyl-NHP-esters
as an alkyl radical donor and quinoxalin-2(1H)-one
derivatives as an alkyl radical acceptor. The operationally simple
protocol works under mild reaction conditions and tolerates a variety
of functional groups. Furthermore, the synthetic utility of the methodology
was successfully implemented for synthesizing biologically relevant
C3-alkyl substituted quinoxalin-2(1H)-one derivatives
We have developed a cerium-photocatalyzed aerobic oxidation of primary and secondary benzylic alcohols to aldehydes and ketones using inexpensive CeCl3·7H2O as photocatalyst and air oxygen as the terminal oxidant.
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