A Radical Addition/Cyclization and Se-Group Transfer Strategy for the Facile Synthesis of Se-Containing Cyclopentenes under Metal-Free and Peroxide-Free Conditions.

A novel intermolecular radical addition/cyclization and Se-group transfer reaction of terminal alkynes and unsaturated alkyl selenide is presented which offers a straightforward and facile approach for the synthesis of valuable Se-containing cyclopentenes. Remarkable features of this strategy include easily accessible starting materials, metal-free and peroxide-free conditions, high atom economy, simple operation and broad substrate scope. More importantly, the reaction is easy to scale up and can be extended to the construction of six-membered carbon ring.

Divergent synthesis of α-functionalized amides through selective N-O/C-C or N-O/C-C/C-N cleavage of aza-cyclobutanone oxime esters.

Herein, a novel sequential ring opening reaction of aza-cyclobutanone oxime esters with isocyanides is described. The reaction proceeded smoothly under redox-neutral and mild conditions, leading to a divergent synthesis of α-cyanomethylaminoamides, α-acyloxyamides and α-acylaminoamides. In these transformations, a selective N-O/C-C or N-O/C-C/C-N cleavage was achieved only by changing the iron-catalyst system.

Amidation-Ketonization-Selenation of Terminal Alkynes Using TEMPO and Elemental Selenium.

Herein, we present a novel silver- or copper-mediated direct amidation-ketonization-selenation of terminal alkynes for the synthesis of α-oxo-selenoamides. The reaction utilized easily accessible elemental selenium as the source of selenium. In addition, the O labeling experiment revealed that TEMPO is the oxygen source of the carbonyl group.

Synthesis of organoselenyl isoquinolinium imides iron(III) chloride-mediated tandem cyclization/selenation of '-(2-alkynylbenzylidene)hydrazides and diselenides.

This report describes the synthesis of organoselenyl isoquinolinium imides through a tandem cyclization between N'-(2-alkynylbenzylidene)hydrazides and diselenides. The reaction was carried out at room temperature under an ambient atmosphere using cheap iron(iii) chloride as the metallic source. The strategy shows good tolerance to a broad range of N'-(2-alkynylbenzylidene)hydrazides and diselenides, and forms C-N and C-Se bonds in one step.