Chemoselective Double Allylic Substitutions with Carbon Nucleophiles: Access to Tetrahydroindoles and Tetrahydrocarbazoles.

A chemoselective double allylic substitution involving two different carbon nucleophiles is described. The reaction relies on a dual catalytic approach, with a Lewis acid promoting the first allylic substitution and Pd promoting the second step. Starting from simple allylic diols, a diversity of polycyclic structures can be obtained, including tetrahydroindole, tetrahydrocarbazole, and tetrahydronaphthalene.

Synthesis and Evaluation of the Photochemical Properties of Heterocyclic Hemiindigos.

This study reports a series of novel heterocyclic hemiindigos (Het-HI) synthesized via the condensation of indoxyl acetate with various heteroaromatic aldehydes. The influence of electron-rich and electron-poor heterocycles on the photochemical and photophysical properties of these compounds has been investigated. Our findings reveal that several Het-HIs exhibit noteworthy photoswitching behavior, including enhanced absorption at the visible region.

Copper-Catalysed Synthesis of (E)-Allylic Organophosphorus Derivatives: A Low Toxic, Mild, Economical, and Ligand-Free Method.

Organophosphorus compounds are fundamental for the chemical industry due to their broad applications across multiple sectors, including pharmaceuticals, agrochemicals, and materials science. Despite their high importance, the sustainable and cost-effective synthesis of organophoshoryl derivatives remains very challenging. Here, we report the first successful regio- and stereoselective hydrophosphorylation of terminal allenamides using an affordable copper catalyst system.

Regio- and Chemoselective Double Allylic Substitution of Alkenyl -Diols.

Double allylic substitution is an attractive approach to building molecular complexity from simple starting materials by creating two new bonds in one pot. However, this type of reaction has been doomed by chemoselectivity and regioselectivity issues. In this letter, we describe a new approach to introduce two new C-C, C-N, C-O, or C-S bonds in a chemo- and regioselective fashion.

Copper-Catalyzed Regio- and Stereoselective Hydrothiolation of Allenamides, Enamides, and Ynamides.

We report a simple protocol for the copper-catalyzed hydrothiolation of N-unsaturated precursors, i.e., allenamides, enamides, and ynamides, under mild conditions.

Easy Access to Allylic Sulfones Through Transition-Metal-Free Hydrosulfonylation Of Allenes.

A Brønsted acid-mediated addition of (hetero)aryl and (cyclo)alkyl sodium sulfinates to -allenyl derivatives, which proceeds in water, is described under very smooth conditions. This reaction provided a practical and efficient protocol for the regio- and stereoselective synthesis of allylic sulfones in an atom- and step-economic fashion.