The efficient synthesis of an 80-member library of unique benzoxathiazocine 1,1-dioxides by a microwave-assisted, intermolecular nucleophilic aromatic substitution (S(N)Ar) diversification pathway is reported. Eight benzofused sultam cores were generated by means of a sulfonylation/S(N)Ar/Mitsunobu reaction pairing protocol, and subsequently diversified by intermolecular S(N)Ar with ten chiral,...

In both solution and the solid phase, a variety of ketone oxime anions have been treated with 4-substituted-2-fluorobenzonitriles to give the corresponding nucleophilic aromatic substitution aryloxime adducts. Under aqueous acidic conditions, these adducts underwent cyclization to give the corresponding ketones. Suzuki and amide coupling reactions were also successfully performed on two resin-b...

A mild and versatile one-pot synthesis of core-expanded naphthalene diimides has been developed, which undergoes a nucleophilic aromatic substitution reaction and then an imidization reaction, allowing an easy and low-cost access to diverse n-type organic materials. Some newly synthesized compounds by this one-pot operation exhibited high electron mobility of up to 0.70 cm(2) V(-1) s(-1) in amb...

Makaluvamine C is a pyrroloiminoquinone which has been isolated from marine sponges. This molecule has been synthesized in 13 steps from p-anisidine. The key steps in this synthesis include an intramolecular nucleophilic aromatic substitution mediated by potassiumtert-butoxide, the selective reduction of a dinitro ester using catalytic hydrogenation, and the novel use of Fremy's salt to synthes...

Reactivity studies of strong organic acids based on the replacement of one or both of the oxygens in benzoic acids with the trifluoromethanesulfonamide group are reported. Novel derivatives of these types of acids were synthesized in good yields. The generated N-triflylbenzamides were further functionalized through cross-coupling and nucleophilic aromatic substitution reactions. All compounds w...

Anionic B complexes have been known and extensively studied as intermediates of nucleophilic aromatic substitution since the beginning of the century.l In a paper that still makes fascinating reading, Meisenheimer describes the formation and isolation of anionic B complexes by reaction of picryl ethers with potassium alkoxides. Structural proof is derived from the fact'that identical u complexe...