Metal-free and PdII-promoted [2+3] cycloadditions of a cyclic nitrone to phthalonitriles: syntheses of oxadiazolines as well as phthalamide-PdII and dihydropyrrolyl-iminoisoindolinone-PdII complexes with high catalytic activity in Suzuki-Miyaura cross-coupling reactions

Chemistry : a European Journal
Jamal LasriArmando J L Pombeiro

Abstract

The previously unknown reactions between phthalonitriles, 1,2-(CN)2(C6)R1R2R3R4 1 (1 a, R1=R2=R3=R4=H; 1 b, R1=R2=R4=H, R3=CH3; 1 c, R1=R4=H, R2=R3=Cl; 1 d, R1=R2=R3=R4=Cl; 1 e, R1=R2=R3=R4=F), and a cyclic nitrone, -O+N==CHCH2CH2CMe2 2, proceed under heating in a sealed tube to give phthalimides 3, 2-oxadiazolyl-benzonitriles 4 or ortho-bis(oxadiazolyl)tetrafluorobenzene 4 e'. In the presence of palladium(II) chloride, phthalonitriles 1 react with 2 at room temperature, to give bis(pyrrolidin-2-ylidene)phthalamide PdII complexes 5 via metal-promoted rupture of the N--O bond of the oxadiazoline ring. The ketoimine ligands thus generated can be liberated from the metal by displacement with a diphosphine. Although the first [2+3] cycloaddition of 2 to 1 can occur in the absence of the metal to give the mono-cycloadducts 4, the second [2+3] coupling at the still-unreacted cyano group requires its activation by coordination to PdII, affording complexes 6 containing two ligated oxadiazolyl-benzonitriles. These ligands undergo either i) further cycloaddition with 2 to afford ultimately (upon rearrangement) the bis(pyrrolidinylidene)phthalamide complexes 5 or ii) N--O bond cleavage in the oxadiazoline ring with intramolecular attack o...Continue Reading

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Citations

Apr 25, 2017·Acta Crystallographica. Section E, Crystallographic Communications·Jamal LasriBandar A Babgi
Dec 5, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Helgi Freyr Jónsson, Anne Fiksdahl
Mar 11, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Andreii S KritchenkovVadim Yu Kukushkin
Mar 11, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Jamal LasriArmando J L Pombeiro
Jul 2, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mohamed M A SolimanArmando J L Pombeiro
Jul 14, 2010·The Journal of Organic Chemistry·Stefan VerbeeckBert U W Maes

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