A Three-Phase Four-Component Coupling Reaction: Selective Synthesis of o-Chloro Benzoates by KCl, Arynes, CO₂, and Chloroalkanes

Abstract

A transition-metal-free three-phase four-component coupling reaction (3P-4CR) involving KCl, arynes, chloroalkanes and CO2 has been reported for the first time, enabling the incorporation of both chloro and CO2 into an aryne simultaneously. The reactions for the synthesis of different types of o-chloro benzoates can be selectively modulated by the chloroalkane utilized. The corresponding products can be alternatively transformed for postsynthetic functionalizations conveniently.

The Versatility of the Aryne–Imine–Aryne Coupling for the ­Synthesis of Acridinium Photocatalysts

“…We began our investigation with the preparation of the Kobayashi aryne precursors 2a – d and imines 3a – d based on the standard literature procedures (Table 1 ). 21 Notably, according to the proposed mechanism for the aryne–imine–aryne coupling, the imine requires sterically demanding substituents near the C-terminus to prevent an undesired 6π-electrocyclization. 20 Therefore, imines with di- ortho -substituted phenyl groups (R 2 ) were synthesized with the consequence that the acridinium salts prepared utilizing this two-step strategy possess a sterically shielded C9 position to further prevent photobleaching via nucleophilic attack or light-promoted radical–radical couplings.…”

Synthesis of Helical and Planar Extended‐Phenanthridinium Salts

“…NMR corresponds to the literature data. [10] Step 2: Prepared according to the literature procedure [23] starting from 10-bromophenanthren-9-ol (1.45 g, 5.31 mmol) to give the product as an orange solid (1.81 g, 4.54 mmol, 86 %). NMR corresponds to the literature data.…”

Rh(III)‐Catalyzed Selective ortho‐C−H Amination of Benzoic Acids with Anthranils: A Facile Access to Anthranilic Acid Derivatives (AAs)

“…5 was obtained in 93 % yield via a halogenexchange reaction of 3 a. [18] Anthranilic acid 6 was synthesized through the hydrolysis of 3 a. Multiple substituted acridine 8 was obtained through intramolecular cyclization of 3 a in TFA at 80°C.…”