N,N,N-Triphenylselenylisocyanuric Acid (TPSCA): A New Versatile Reagent for α-Phenylselenenylation of Aldehydes and Ketones

Abstract

A new, versatile reagent, N,N,N-triphenylselenyl-isocyanuric acid (TPSCA) has been prepared, characterized, and used as a source of the electrophilic phenylselenyl group. This relatively stable compound was utilized for an efficient α-selenenylation reaction of aldehydes and ketones catalyzed by L-prolinamide under mild reaction conditions. The organocatalytic asymmetric α-selenenylation of an aldehyde was also studied and the reaction was found to proceed with high enantioselectivity (96% ee).

A Novel Synthesis of Highly Functionalized 1,2,4-Diselenazolidines from Acyl Isoselenocyanates

“…The current interest in the chemistry of selenium-containing compounds is mainly due to their pharmaceutical 4,5 and synthetic applications. [6][7][8] Acyl isoselenocyanates are useful intermediates for the preparation of selenium-containing heterocycles, as they are more stable and less toxic than other reagents. [9][10][11] Acyl isoselenocyanate intermediates are readily prepared by the reaction of acyl chlorides with KSeCN, a method first described by Douglas.…”

Trichloroisocyanuric Acid‐Promoted Synthesis of Arylselenides and Aryltellurides from Diorganyl Dichalcogenides and Arylboronic Acids at Ambient Temperature

“…It has been reported that diorganyl dichalcogenides can be cleaved by N ‐haloimides to form corresponding organochalcogeno halides and N ‐organochalcogeno‐substituted imide derivative [29] . Then, we tested coupling reactions of 4‐methylphenyl boronic acid ( 2 a ) with phenyl selenium chloride ( 9 ) and N , N , N ‐triphenylselenylisocyanuric acid ( 10 ) under the identified reaction conditions [30] . These two reactions afforded 3 aa only in 30% and 42% yields, respectively.…”

Recent Progress on Alkyl-, Aryl- and Fluoroalkyl-selenylation Reactions

“…2013 年, Lenardão 课题组 [59] 报道了在氮气保护下, [65] . 2018 年, 我们课题组 [66] 2013 年, Greaney 课题组 [68] 报道了苯硒酚与氯二氟 甲基乙酸钠在碳酸钾作用下, 于 95 ℃下, 在 DMF 中反 应 8 h, 以 65%的产率得到二氟甲硒基化产物(Scheme 32).…”