Pyrimidine as an Aryl C–H Activating Group

Abstract

The Pd-catalyzed regioselective C-H activation/arylation, /iodination, and/acetoxylation reactions of 4-arylpyrimidines using aryl iodides, N-iodosuccinimide, and (diacetoxyiodo)benzene respectively as coupling partners are described. Suzuki-Miyaura coupling and Sonogashira reactions of the resulting aryl iodides are demonstrated. The scalability of the C-H activation/functionalization starting with readily accessible 4-aryl pyrimidines is also reported.

Charge‐Transfer and Arrangement Effects on Delayed Photoluminescence from Phthalimide Cocrystals

“…4-Bromophthalimides 1a-c were prepared by using condensation reactions of 4-bromophthalic anhydridew ith the corresponding arylamine derivatives in DMF (1a [18] and 1c [19] are known compounds). We found that the 4-dimethylaminophthalimides 2a--c were produced as side-products in the reactions, respectively.I na ll cases,t hese substances can be separated by using column chromatography on SiO 2 .R egarding the mechanism of the formation of 2,w ep ropose that under reflux conditions DMF reacts with arylamine derivatives to liberate dimethylamine.…”

“…Phthalimide derivatives are promisinga so rganic optical materials. [15][16][17][18][19] These substances are thermally stable and capable of undergoing n-p*e lectronic transitions owing to the presence of carbonyl groups. Linked D-A-type phthalimidesa nd their p-extended derivatives can generate stable intramolecular charge-transfer( ICT) states, which are responsible for colour tuneable and highly efficient PL properties.I na ddition to their widely applicable opticalproperties, simple phthalimide derivatives are suitable to investigate the relation between their crystal structures and photochemical properties.…”

Applications of Phenyliodine(III)diacetate in C−H Functionalization and Hetero‐Hetero Bond Formations: A Septennial Update

“…The N ‐hydroxyimide/I 2 /hypervalent iodine oxidant system was suggested by Terent'ev and co‐workers for the iodo‐oxyimidation of styrenes ( 205 ) (Scheme 72). [152] It was demonstrated that a variety of nucleophiles might substitute for the iodine atom in the synthesized iodo‐oxyimides ( 207 ). The key attribute of the developed process was the non‐standard regioselectivity of C−I and C−O bond production, which suggested the radical reaction route.…”

Regioselective C-H Functionalization of the Six-Membered Ring of the 6,5-Fused Heterocyclic Systems: An Overview

“…In various reported studies, the regioselectivities of C-H and C-H/C-H activations were controlled by DG such as monodentate amides [ 13 , 14 ], carboxylic acids [ 15 ], ketones [ 15 , 16 , 17 ], nitriles [ 18 , 19 ], aldehydes [ 15 , 20 ], phenols [ 21 , 22 ], esters [ 15 , 16 , 23 ], amides [ 15 , 16 ], N- methoxybenzamide [ 24 ], ureas [ 25 , 26 ], imines [ 27 , 28 ], hydrazines [ 29 , 30 ] and hydrazones [ 31 ], bidentate ligands [ 6 ], carbamates [ 32 ], sulfoxides [ 33 ], sulfonamides [ 34 , 35 ], sulfoximines [ 36 ], phosphine oxides [ 37 , 38 ], sulfides [ 39 ], thioamides [ 40 ] as well as some heterocycles such as purines [ 41 ], pyrimidines [ 42 ], pyrazoles [ 43 , 44 ], oxazolines [ 44 ], azoles [ 45 ], benzothiazoles [ 46 ], oxadiazoles [ 47 ], benzoxazoles [ 48 , 49 ] and 7-azaindole [ 50 ]. In some cases, heterocycles such as pyridine- N- oxide [ 51 ,…”