Light‐Mediated Seleno‐Functionalization of Organic Molecules: Recent Advances

Abstract

Organoselenium compounds constitute an important class of substances with applications in the biological, medicinal and material sciences as well as in modern organic synthesis, attracting considerable attention from the scientific community. Therefore, the construction of the C−Se bond via facile, efficient and sustainable strategies to access complex scaffolds from simple substrates are an appealing and hot topic. Visible light can be regarded as an alternative source of energy and is associated with environmentally‐friendly processes. Recently, the use of visible‐light mediated seleno‐functionalization has emerged as an ideal and powerful route to obtain high‐value selenylated products, with diminished cost and waste. This approach, involving photo‐excited substrates/catalyst and single‐electron transfer (SET) between substrates in the presence of visible light has been successfully used in the versatile and direct insertion of organoselenium moieties in activated and unactivated C(sp3)−H, C(sp2)−H, C(sp)−H bonds as well as C−heteroatom bonds. In most cases, ease of operation and accessibility of the light source (LEDs or commercial CFL bulbs) makes this approach more attractive and sustainable than the traditional strategies.

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

“…All these advantages have meant that in the last seven years there has been a significant increase in the number of works reporting the use of photochemistry in the seleno-functionalization of several classes of organic substrates [ 70 ]. For example, the carbon-selenium bond formation in heteroarene-like indoles [ 71 , 72 ], imidazo[1,2 a ]pyridines [ 73 , 74 ], coumarines [ 75 ], benzothiazoles [ 76 ] and pyridines [ 77 ]; selenylation of naphthols [ 78 ], terminal alkenes [ 79 , 80 ] and alkynes [ 81 , 82 ] and sp 3 carbons [ 83 , 84 ]; and selenocyclization reactions have been reported [ 85 , 86 ].…”

Clarification on the Reactivity of Diaryl Diselenides toward Hexacyclohexyldilead under Light

“…In recent years, several photochemical C-Se bond formation reactions have been reported [ 34 , 35 , 36 , 37 , 38 , 39 , 40 ]. The use of photocatalysts is one of the effective methods to achieve this type of transformation under visible light irradiation [ 34 , 35 ].…”

Recent Developments in the Photochemical Synthesis of Functionalized Imidazopyridines

“…Selenylated molecules have attracted great interest in chemistry, namely by their biological and medicinal properties including anticancer or anti-Alzheimer’s activities. They also represent key synthetic intermediates/substrates in total synthesis or asymmetric catalysis [ 87 ]. The synthesis of organoselenium compounds has been an important topic in organic chemistry with their rising importance.…”