tert-Butoxide-Mediated Arylation of 1-Acetylindolin-3-ones with Diaryliodonium Salts

Abstract

A procedure for the 2-arylations of indolinone derivatives with diaryliodonium salts mediated by potassium tert-butoxide is developed. Various monoarylated indolinone derivatives are readily obtained in 24-70% yield via this method. The alkylation of monoarylated indolinone derivatives with allyl bromide or benzyl bromide affords the corresponding 2,3-disubstituted products in 60% and 70% yield, respectively.

Transition-Metal-Free Direct C–H Arylation of Quinoxalin-2(1H)-ones with Diaryliodonium Salts at Room Temperature

“…In recent years, iodine­(III) compounds have been widely studied as mild and environmentally benign agents in modern synthesis because of their advantages, which include good availability, good stability, low toxicity, high reactivity, easy handling, and good tolerance of diverse functional groups. , Recently, diaryliodonium salts have been employed particularly as arylating agents in various methodologies, − even in transition-metal-free reactions . Nevertheless, in these approaches for aryl–aryl bonds formation, most substrates coupled with diaryliodonium salts were electron-rich or unbiased arenes. − In addition, high temperatures were required during these processes .…”

Total Synthesis of Calanthoside, a Potential Hair Growth Stimulant: A Facile Synthetic Approach via One-Pot S- and O-Glucosidic Bond Formation

“…Therefore, this reaction was speculated to proceed mainly via an S N 1-like process, in which the cooperative action of BF 3 ·Et 2 O and HFIP facilitated the formation of the C , N -diacyliminium cation A , followed by trapping A with the sulfhydryl group of 10b . Reaction in toluene, which gave 18b and 18c , fully supported this hypothesis (entry 16). After determining the optimal solvent, the potency of Lewis acids, such as TMSOTf, AlCl 3 , SnCl 4 , and TiCl 4, and Brønsted acids, such as PTSA, HBF 4 ·Et 2 O, and H 2 SO 4 , were evaluated.…”

“…The extract was washed with brine (20 mL) and concentrated in vacuo. The residue was purified by column chromatography ( n -hexane/EtOAc = 3:1) to give a pale yellow oil including a ca 3:1 mixture (79 mg, 0.30 mmol, 46%) consisting of 1-acetyl-2-(4-methylphenyl)­indolin-3-one ( 18b ) and 1-acetyl-2-(2-methylphenyl)­indolin-3-one ( 18c ) together with 8 (0.12 g, 0.22 mmol, 34%). The product distribution was determined by 1 H NMR spectrum (600 MHz) of the mixture of 18b and 18c .…”

Diaryliodonium Salts in Organic Syntheses: A Useful Compound Class for Novel Arylation Strategies

“…The C2-arylation of indolinone derivatives 74 was recently described by Zhang et al 61 They also used potassium tert-butoxide as the base in their transformations, and the reactions were conducted in tetrahydrofuran at 30 °C (Scheme 30). Various 2-arylated products 75 were synthesized, although moderate yields were achieved.…”