Halides copper-catalyzed coupling

Allyl vinyl ethers may be prepared via stereospecific copper-catalyzed coupling of allyl alcohols and vinyl halides. For example, the copper catalyst derived from the tetramethyl 1,10-phenanthroline ligand shown below facilitates C-0 bond formation between ( )-vinyl iodides and allyl alcohols when the reaction mixture is heated in the presence of air. ... 

Okuro, K., Furuune, M., Miura, M., Nomura, M. Copper-catalyzed coupling reaction of aryl and vinyl halides with terminal alkynes. 

Ma and coworkers242 noticed the accelerating effect of a-amino acids in the copper-catalyzed coupling reactions of aryl halides with a-amino acids using Cul as catalyst and K2CO3 as base. The authors noted that the coupling reaction of bromobenzene with L-... 

Interest in copper-catalyzed coupling reactions has resurged due to the economic attractiveness of copper. Two different groups described the use of copper as a catalyst for efficient arylation reactions. Cristau and Taillefer detailed a mild copper-catalyzed N- and C-arylation with aryl bromides and iodides with various substrates <04CEJ5607>. One reaction examined was A -arylation of 2-pyridones. Li et al. has explored the copper-catalyzed coupling reaction of 2-pyridones 27 with aromatic halides 28 based on Buchwald s protocol to prepare N-aryl-2-pyridones 29 <04TL4257> as shown in Scheme 12. 

Although thiols are generally stronger nucleophiles than alcohols and amines, the sensitivity of sulfides towards oxidation as well as the formation of disulfide made the cross-coupling between aryl halides and thiols difficult. From all previously reported results, it was foimd that only aryl iodides were suitable for this copper-catalyzed coupling process. 

Copper-catalyzed couplings of phenols with aryl halides. 2-(3 ,4 -Dimethyl-phenoxy)benzoic acid ... 

Copper-Catalyzed Coupling of Amides with Aryl Halides... 

Copper-Catalyzed Coupling of Aryl Halides with Alcohols and Thiols... 

Some of the advantages of copper catalysts are that they are inexpensive, abundant etc. In 2013, Fu, Peters and their co-workers reported a copper-catalyzed coupling of aryl halides with thiols via a single-electron transfer pathway. In order to prove the reaction mechanism, they performed the reaction of allyl-o-iodophenol with thiophenol as well. No cyclized product could be produced when the reactions were performed in the dark, while 57% of dihydrobenzofuran was formed when hv was introduced (Scheme 2.40). 

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