Highly Efficient Route to Diselenides from the Reactions of Imines and Selenium in the Presence of Carbon Monoxide and Water

Abstract

Reactions of selenium with imines (RR 1 C ¼ NR 2 ) of aldehydes and ketones in the presence of carbon monoxide, water and triethylamine lead to reductive selenation, on aerobic work-up, to afford symmetrical diselenides (RR 1 CHSe) 2 in good to excellent yields. The proposed mechanism suggests that both in situ generated carbonyl selenide (SeCO) and hydrogen selenide (H 2 Se) are involved in the reaction.

Recent Advances in Organoselenium Chemistry

“…Although there are many different syntheses available for selenium-containing compounds, different novel procedures have emerged to prepare such derivatives more easily and under milder reaction conditions. Diselenides can be prepared reductively from either aldehydes [45] or imines [46] in the presence of carbon monoxide as shown in Scheme 18.…”

Ruthenium(III) Chloride Catalyzed Efficient Synthesis of Unsymmetrical Diorganyl Selenides via Cleavage of Dibenzyl and Diphenyl Diselenides in the Presence of Zinc

“…During our ongoing investigation on catalytic selenation, we have recently developed two very efficient procedures to synthesize symmetrical dibenzyl diselenides from the reactions of aldehydes10a or imines of aldehydes and ketones 10b with elemental selenium in the presence of CO and water. Development of efficient catalytic procedures to cleave these diorganyl diselenides to unsymmetrical benzylselenides was one of our goals.…”

A Simple Zinc-Mediated Method for Selenium Addition to Michael Acceptors

“…Diphenyl diselenide 1 is commercially available, whereas diselenide 32 was prepared according to the procedure reported in the literature [69]. Selenocystine is commercially available and it was Nand O-protected, according to the procedure reported in the literature [70] in order to obtain compound 33.…”