106593-44-6Relevant academic research and scientific papers
The direct arylation of benzoquinones with arylboronic acid promoted by iron(II) oxalate
Huanga, Yibo,Guanb, Dan
, p. 649 - 651 (2013)
Arylations of various quinones with several arylboronic acids have been developed. The reactions proceed readily at ambient temperature using iron(II) oxalate as a catalyst and potassium persulfate as a co-oxidant. The mechanism is presumed to proceed through a nucleophilic radical addition to the quinone with in situ reoxidation of the resulting dihydroquinone.
Mn-Catalyzed 1,6-conjugate addition/aromatization of: Para -quinone methides
Yang, Bobin,Yao, Wei,Xia, Xiao-Feng,Wang, Dawei
supporting information, p. 4547 - 4557 (2018/06/29)
A series of ferrocenyl triazole ligands have been synthesized and characterized, which proved to be effective for the Mn-catalyzed 1,6-conjugate addition/aromatization of para-quinone methides with good to high yields under mild conditions. This protocol provided an efficient and practical route to the synthetically interesting functionalized quinones, methines and their analogues.
Catalytic asymmetric [2+2] cycloaddition between quinones and fulvenes and a subsequent stereoselective isomerization to 2,3-dihydrobenzofurans
Zheng, Haifeng,Xu, Chaoran,Wang, Yan,Kang, Tengfei,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming
supporting information, p. 6585 - 6588 (2017/07/10)
The catalytic enantioselective [2+2] cycloaddition between quinones and fulvenes was achieved, for the first time, by the use of a chiral copper(ii) complex catalyst. The transformation afforded a series of enantiomerically enriched [6,4,5]-tricyclic cyclobutane derivatives in good yields with excellent regio- and stereoselectivities. Furthermore, the [2+2] adducts could be easily converted into formal [3+2] adducts efficiently and stereoselectively.
Ir-catalyzed arylation, alkylation of quinones with boronic acids through C-C coupling
Wang, Dawei,Ge, Bingyang,Ju, Anqi,Zhou, Yucheng,Xu, Chongying,Ding, Yuqiang
supporting information, p. 30 - 33 (2015/01/30)
Ir-catalyzed arylation, alkylation of quinones with boronic acids was developed under room temperature. Both aryl and alkyl boronic acids are suitable for this transformation. This expands the application scope of the iridium catalyst. This is also an excellent proof that iridium catalysts can be used in the C-C coupling of quinones and naphthoquinones with alkyl boronic acids.
Synthesis of aryl- and alkylquinones through rhodium-catalyzed C-C coupling under mild conditions
Wang, Dawei,Ge, Bingyang,Du, Liyong,Miao, Hongyan,Ding, Yuqiang
supporting information, p. 2895 - 2898 (2015/02/02)
A direct arylation, alkylation of quinones with aryl and alkyl boronic acids through rhodium-catalyzed C-C coupling has been developed under mild conditions. [CpRhCl2]2 was shown to be the most effective catalyst for the transformation. More importantly, good to excellent yields were obtained under room temperature and base-free conditions. This reaction provides a practical, efficient method for the synthesis of aryl- and alkylquinones.
Transition metal-free direct C-H functionalization of quinones and naphthoquinones with diaryliodonium salts: Synthesis of aryl naphthoquinones as β-secretase inhibitors
Wang, Dawei,Ge, Bingyang,Li, Liang,Shan, Jie,Ding, Yuqiang
, p. 8607 - 8613 (2015/01/08)
A novel ligand-free, transition metal-free direct C.H functionalization of quinones with diaryliodonium salts has been developed for the first time. The transformation was promoted only through the use of a base and gave aryl quinone derivatives in moderate to good yields. This methodology provided an effective and easy way to synthesize β-secretase inhibitors. The radical trapping experiments showed that this progress was the radical mechanism.
FeSO4-promoted direct arylation of benzoquinones with ArB(OH)2 or ArBF3K
Komeyama, Kimihiro,Kashihara, Tetsuya,Takaki, Ken
supporting information, p. 1084 - 1086 (2013/04/10)
FeSO4·7H2O was proven to work as effective promoter for the direct arylation of benzoquinones with aryl boronic acids in the presence of K2S2O8. In the arylation, slow addition of iron solution was crucial to efficiently proceed with the reaction. Interestingly, the Fe-mediated arylation could be converted into a catalytic reaction by using hydroquinones, instead of benzoquinones, or addition of ascorbic acid.
Iron-mediated direct arylation with arylboronic acids through an aryl radical transfer pathway
Wang, Jian,Wang, Shan,Wang, Gao,Zhang, Ji,Yu, Xiao-Qi
supporting information, p. 11769 - 11771 (2013/01/15)
A novel iron-mediated direct C-H arylation of quinones and pyridine analogues with arylboronic acids has been developed using dichloromethane and water as solvents at ambient temperature. FeS is employed and serves as an efficient catalyst. A detailed reaction mechanism is speculated and expounded.
Practical C-H functionalization of quinones with boronic acids
Fujiwara, Yuta,Domingo, Victoriano,Seiple, Ian B.,Gianatassio, Ryan,Del Bel, Matthew,Baran, Phil S.
supporting information; experimental part, p. 3292 - 3295 (2011/05/03)
A direct functionalization of a variety of quinones with several boronic acids has been developed. This scalable reaction proceeds readily at room temperature in an open flask using inexpensive reagents: catalytic silver(I) nitrate in the presence of a persulfate co-oxidant. The scope with respect to quinones is broad, with a variety of alkyl- and arylboronic acids undergoing efficient cross-coupling. The mechanism is presumed to proceed through a nucleophilic radical addition to the quinone with in situ reoxidation of the resulting dihydroquinone. This method has been applied to complex substrates, including a steroid derivative and a farnesyl natural product.
