Abstract
A series of N-aryl-N-(2-oxo-2-arylethyl) benzamides and cinnamides has been prepared. The reaction of the benzamides with Woollins’ reagent, a highly efficient chemoselective selenation/reduction reagent, gave the corresponding N-aryl-N-(arylenethyl) benzoselenoamides in good yields. Five representative single crystal X-ray structures are discussed.
Highlights
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2,4-Bis-1,3-diselenadiphosphetane-2,4-diselenide (Woollins’ reagent, WR) has played a role in synthetic chemistry in the past two decades [1,2,3,4,5,6,7,8,9,10,11,12,13]. It has been successfully applied as an efficient building unit to synthesize a series of eight, nine, and ten-membered selenophosphorus heterocycles with P-Se-Se-P linkage [14], as well as unique octaselenocyclododecane with four carbon atoms and eight selenium atoms in this twelve-membered cycle [15]
Another attractive application has been that it acts as a highly chemoselective reagent, e.g., the reduction of a wide range of 1,4-enediones and 1,4-ynediones in methanol led to saturated 1,4-diketones [16] and the selective reduction of the double bond of 2-α,β-unsaturated thiazo- and selenazolidinones gave the corresponding saturated heterocycles [17]
Summary
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. Introduction 2,4-Bis (phenyl)-1,3-diselenadiphosphetane-2,4-diselenide (Woollins’ reagent, WR) has played a role in synthetic chemistry in the past two decades [1,2,3,4,5,6,7,8,9,10,11,12,13] It has been successfully applied as an efficient building unit to synthesize a series of eight-, nine-, and ten-membered selenophosphorus heterocycles with P-Se-Se-P linkage [14], as well as unique octaselenocyclododecane with four carbon atoms and eight selenium atoms in this twelve-membered cycle [15]. To continue our interest in the chemistry of Woollins’ reagent towards various organic substrates, we report an investigation on the use of WR as a selenation/reduction reagent for transferring N-aryl-N-(2-oxo-2-arylethyl) benzamides into the corresponding N-aryl-N-(arylenethyl) benzoselenoamides
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