Copper‐Catalyzed Sonogashira‐Cross‐Coupling of Phenols Using Dichloroimidazolidinedione

Abstract

Phenols are considered as an ideal alternative to aryl halides as coupling partners in cross-coupling reactions. In this work a copper-catalyzed Sonogashira cross-coupling of phenols using Dichloroimidazolidinedione (DCID) as new CÀ O activation agent has been developed for the first time. Substituted phenols and phenyl acetylenes were well-matched with the optimizing reaction conditions.

Copper-catalyzed Sonogashira reactions: advances and perspectives since 2014

“…Hosseini and co-workers proposed a copper-catalyzed Sonogashira cross-coupling reaction in presence of dichloroimidazolidinedione (DCID). 24 This method involves the reaction between substituted phenols and phenyl acetylenes. Phenols with electron-donating groups in para , ortho , and meta position and disubstituted phenols efficiently gave the desired product in good yields.…”

DCID-mediated Heck cross-coupling of phenolsviaC–O bond activation

“…[10][11][12] However, there are limited reports for the palladium catalyzed Heck coupling of activated C-O bonds in phenols in the literature and the development of a more consistent and general direct method for Pd-catalyzed Heck cross-coupling of activated C-O bonds in phenols has been readily expected. Recently, we have reported the use of DCID as an efficient reagent for the C-O activation of phenol in the CuI-catalyzed Narylation of amines, 13 CuI-catalyzed Sonogashira cross coupling of acetylenes 14 and Pd@MOF-catalyzed Suzuki cross coupling of aryl boronic acids. 15 Encouraged by these results, again we have used DCID as an efficient activating agent in the Pd(PPh 3 ) 4 catalyzed Mizoroki-Heck cross-coupling reaction between phenol and styrene in CH 3 CN at 80 1C under aerobic conditions (Scheme 1).…”