Synthesis of Borophosphonate Cage Compounds: Influence of Substituent and Concentration Effects on Product Distribution in Condensation Reactions of Aryl Phosphonic Acids and Boronic Acids
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资源简介：
Aryl
borophosphonate cage compounds [ArPO3BAr′]n with n = 4 or 6 were synthesized by condensation reactions of
ArP(O)(OH)2 and Ar′B(OH)2. (3,5-tBu2-Ph)P(O)(OH)2 (1) reacts with arylboronic acids that contain electron-withdrawing
substituents to form borophosphonate tetramers [Ar1PO3BAr2]4 (Ar1 = 3,5-tBu2-Ph; Ar2 = o-Br-Ph, o-CF3-Ph, p-CF3-Ph, p-CHO-Ph; 3a–d) and hexamers [Ar1PO3BAr2]6 (Ar2 = p-CF3-Ph, p-CHO-Ph; 4c–d) in 80–93% NMR yield. For Ar2 = p-CF3-Ph and p-CHO-Ph, both products were
observed, with the tetramer being favored under dilute reaction conditions
and the hexamer favored under concentrated reaction conditions. Interconversion
between tetramer (3c or 3d) and hexamer
(4c or 4d) was observed at room temperature
and above in toluene. The phosphine phosphonic acid (2-PPh2-Ph)P(O)(OH)2 (6) reacts with arylboronic
acids that contain electron-withdrawing substituents to form tetramers
[Ar1PO3BAr2]4 (Ar1 = 2-PPh2-Ph; Ar2 = p-CF3-Ph, p-CHO-Ph; 7c–d) in 70–75% NMR yield. The reactions of 1 or 6 with (p-tolyl)B(OH)2 (2f), and the reaction of 6 with (o-CF3-Ph)B(OH)2 (2b),
yield only trace amounts of borophosphonate cage compounds and instead
afford the corresponding [ArBO]3 boroxines and condensation
products with unknown structures.
创建时间：
2016-02-16
