Visible-Light Mediated Diarylselenylative Cyclization of 1,6-Enynes

Abstract

We herein described a selenylative cyclization reaction of enynes by the utilization of diselenides as radical sources. The visible-light irradiation of the reaction mixture enables the generation of the selenium atom radical to trigger the radical addition/cyclization/selenation sequences. Both terminal alkyne and internal alkyne derived 1,6-enynes were tested and suitable for the current synthetic protocol, delivering various kinds of seleniumcontaining cycles in good yields.

Synthesis of Selenaheterocycles via Visible‐Light‐Mediated Radical Cyclization

“…Based on the abovementioned observations and previous studies, [5,9b,c] a plausible reaction mechanism is depicted in Scheme 5. Initially, aryl selenocyanate I is generated in situ by aryl diazonium salt 1 a and KSeCN.…”

“…These compounds possess significant biological activities such as antitumor, [1] antiviral, [2] antioxidant, [3] and antimicrobial properties [4] . Moreover, they can act as electron donors or hydrogen bond acceptors because of the unique electronegativity of the selenium atom [5,6] . Therefore, they have been broadly employed for the preparation of pharmaceuticals, agricultural chemicals, catalysis, ligands, and functional organic materials [6] .…”

Photoinduced Phosphorylation/Cyclization of Cyanoaromatics for Divergent Access to Mono- and Diphosphorylated Polyheterocycles

“…Unfortunately, the regio- and chemoselective phosphorylation/cyclization reaction involving a cyano group to synthesize more structurally diverse phosphorylated polyheterocycles through visible-light-induced pathways is challenging . Herein, we report the switchable and facile photocatalytic phosphorylation of cyanoaromatics with the 1,6-enyne moiety for the diverse and selective synthesis of potentially bioactive phosphorylated polyheterocycles, including not only phosphorylated ketones but also unprecedented phosphorylated aminophosphonates and iminophosphonates (Scheme b).…”

Stereo- and Regioselective cis-Hydrophosphorylation of 1,3-Enynes Enabled by the Visible-Light Irradiation of NiCl2(PPh3)2

“…In continuing our research program on visible-light photochemistry, as well as alkenyl phosphine oxide synthesis, we describe the visible-light-driven nickel-catalyzed stereo- and regioselective cis -hydrophosphorylation of 1,3-enynes that accesses various ( E )-1,3-dienes without using an added photocatalyst (Scheme c).…”