113555-98-9Relevant academic research and scientific papers
A new route to seleno and telluro esters by Co2(CO)8-mediated and -catalyzed carbonylation of diaryl diselenides and ditellurides with carbon monoxide
Uemura, Sakae,Takahashi, Hidetaka,Ohe, Kouichi,Sugita, Nobuyuki
, p. 63 - 72 (1989)
Diaryl Diselenides react with CO(5-100 atm) at 100-200°C during 1-4 h in the presence of Co2(CO)8 to give the corresponding aryl selenocarboxylic acid esters in 21-96% yields. Similar treatment of diphenyl ditelluride gives the telluro analogues in lower yields. Didodecyl diselenide also gives the corresponding seleno ester, while esters were not produced from dibenzyl diselenide and didodecyl ditelluride. Under milder conditions (10 atm CO/125°C/1 h) the reactivity of (PhM)2 (M S, Se, Te) for the corresponding esters was found to be in the order Te > Se > S. The carbonylation of diaryl diselenides proceeds catalytically in Co2(CO)8 in the presence of triphenylphosphine. It was shown unambiguously that benzoylcobalt tetracarbonyl, which is one of the possible intermediates when aryl is phenyl, reacts smoothly with diphenyl diselenide or ditellutide to give the corresponding ester, phenyl selenobenzoate or tellurobenzoate, respectively, in a good yield.
Palladium-Catalyzed Carbonylative Synthesis of Aryl Selenoesters Using Formic Acid as an Ex Situ CO Source
Yano De Albuquerque, Danilo,Teixeira, Wystan K. O.,Sacramento, Manoela Do,Alves, Diego,Santi, Claudio,Schwab, Ricardo S.
, p. 595 - 605 (2022/01/12)
A new catalytic protocol for the synthesis of selenoesters from aryl iodides and diaryl diselenides has been developed, where formic acid was employed as an efficient, low-cost, and safe substitute for toxic and gaseous CO. This protocol presents a high functional group tolerance, providing access to a large family of selenoesters in high yields (up to 97%) while operating under mild reaction conditions, and avoids the use of selenol which is difficult to manipulate, easily oxidizes, and has a bad odor. Additionally, this method can be efficiently extended to the synthesis of thioesters with moderate-to-excellent yields, by employing for the first time diorganyl disulfides as precursors.
