20743-91-3Relevant articles and documents
Copper-catalyzed hydroxylation of aryl halides: Efficient synthesis of phenols, alkyl aryl ethers and benzofuran derivatives in neat water
Wang, Yangxin,Zhou, Chunshan,Wang, Ruihu
, p. 3910 - 3915 (2015)
A thorough study of environmentally friendly hydroxylation of aryl halides is presented. The best protocol consists of hydroxylation of different aryl bromides and electron-deficient aryl chlorides by water solution of tetrabutylammonium hydroxide catalyzed by Cu2O/4,7-dihydroxy-1,10-phenanthroline. Various phenol derivatives can be obtained in excellent selectivity and great functional group tolerance. This methodology also provides a direct pathway for the formation of alkyl aryl ethers and benzofuran derivatives in a one-pot tandem reaction.
Unprecedented Regioregular Poly(1,4-arylene)s Prepared by Nickel(II)-Catalyzed Cross-Coupling Polymerization of 2,5-Disubstituted Bromo(chloro)arylene
Shibuya, Yushin,Nakagawa, Naoki,Miyagawa, Naoki,Suzuki, Toyoko,Okano, Kentaro,Mori, Atsunori
supporting information, p. 9547 - 9550 (2019/06/24)
The unprecedented synthesis of regioregular head-to-tail-type poly(1,4-arylene)s bearing different substituents at the 2- and 5-positions is described. They were prepared by the polymerization of 2,5-disubstituted bromo(chloro)arylenes by selective halogen–metal exchange with a Grignard reagent and subsequent cross-coupling polymerization with a nickel catalyst [NiCl2(dppp)]. Formation of the regioregular poly(1,4-arylene)s were confirmed by NMR spectroscopy, and showed remarkable differences to those polymers having uncontrolled regioregularity. Polymerization of bromo(chloro)arylenes with a chiral alkoxy substituent also led to the regioregular head-to-tail-type polyarylene, which demonstrated circular dichroism, thus suggesting formation of a structure with higher-order regularity.
Copper and l-sodium ascorbate catalyzed hydroxylation and aryloxylation of aryl halides
Song, Guang-Lin,Zhang, Zhang,Da, Yu-Xia,Wang, Xi-Cun
, p. 8823 - 8829 (2015/10/20)
CuSO4·5H2O and NaAsc catalyzed hydroxylation and C-O/C-S cross-coupling reactions of aryl halides with phenols or 4-methylbenzenethiol were described. A wide range of substrates and test cases highlight the synthetic utility of the approach. A series of phenols, diaryl ethers, alkylaryl ethers, and diaryl thioethers were synthesized in high yield.