106501-69-3Relevant academic research and scientific papers
Lewis Acid Regulated Divergent Catalytic Reaction between Quinone Imine Ketals (QIKs) and 1,3-Dicarbonyl Compounds: Switchable Access to Multiple Products Including 2-Aryl-1,3-Dicarbonyl Compounds, Indoles, and Benzofurans
Chen, Xingyu,Lu, Sixian,Deng, Ping,Chang, Xiaoqiang,Zhao, Yifan,Ma, Yue,Zhang, Dong,Xia, Fei,Yang, Lan,Wang, Jigang,Sun, Peng
supporting information, p. 94 - 102 (2021/10/05)
A catalytic Lewis acid regulated reaction between quinone imine ketals (QIKs) and 1,3-dicarbonyl compounds provides a divergent and tunable approach to a variety of skeletons, including a series of 2-aryl-1,3-dicarbonyl compounds, indoles, and benzofurans. The use of lithium chloride and ferrous bromide gives C3- or C2-alkylation products of the QIKs. The combination of ferrous bromide and trifluoromethanesulfonic acid delivers indole derivatives. Sequential hydrolysis and C3-alkylation occur in the presence of ytterbium (III) trifluoromethanesulfonate and stoichiometric amounts of water. When the reaction is performed with trifluoromethanesulfonic acid and stoichiometric amounts of water, benzofuran is obtained. This protocol utilizes mild conditions, exhibits regio- and chemoselectivity, and has broad functional group tolerance. (Figure presented.).
Transition-Metal-Free Regioselective One-Pot Synthesis of Aryl Sulfones from Sodium Sulfinates via Quinone Imine Ketal
Halder, Priyanka,Humne, Vivek T.,Mhaske, Santosh B.
, p. 1372 - 1378 (2019/01/30)
A novel, efficient, and regioselective transition-metal-free one-pot synthesis of aryl sulfones via the reactive quinone imine ketal intermediate is demonstrated using easily accessible bench-stable sulfinate salts. A broad range of functionality on p-ani
Highly chemo- and regioselective C-P cross-coupling reaction of quinone imine ketals with Ar2P(O)H to construct: Ortho -amino triarylphosphine derivatives
Liu, Teng,Li, Yongqin,Cheng, Feixiang,Shen, Xianfu,Liu, Jianjun,Lin, Jun
supporting information, p. 3536 - 3541 (2019/07/10)
A highly chemo- and regioselective approach for the construction of ortho-amino triarylphosphine oxides has been achieved through a C-P cross-coupling reaction involving quinone imine ketals (QIKs) with Ar2P(O)H and catalyzed via a Lewis base. This alternative protocol provided a wide substrate scope with excellent yields (82-95%), and a variety of ortho-amino triarylphosphines were obtained with high yields (87-95%) via further reductive reaction. Furthermore, this reaction could be scaled-up and several synthetic transformations were accomplished for the construction of functionalized organophosphorus.
Lewis Base Promoted, Direct 1,4-Conjugate Addition to Quinone Imine Ketals: Efficient Access to Unsymmetrical Diaryl Sulfones
Liu, Teng,Liu, Jianjun,Shen, Xianfu,Xu, Jianbin,Nian, Beifang,He, Ni,Zeng, Shunqun,Cheng, Feixiang
, p. 1365 - 1376 (2019/03/08)
An alternative approach with eco-friendliness and high efficiency for the preparation of unsymmetrical diaryl sulfones has been developed. The strategy takes advantage of the reaction of sulfonyl hydrazides with quinone imine ketals catalyzed by DABCO (triethylenediamine) in ethanol. This transformation proceeds via a Lewis base promoted, direct 1,4-conjugate addition/sulfonylation/alcohol elimination reaction sequence. The protocol provides an efficient approach to access an array of diverse unsymmetrical diaryl and heterodiaryl sulfones, aryl alkyl sulfones and aryl vinyl sulfones in good to excellent yields.
Axially chiral dicarboxylic acid catalyzed activation of quinone imine ketals: Enantioselective arylation of enecarbamates
Hashimoto, Takuya,Nakatsu, Hiroki,Takiguchi, Yuka,Maruoka, Keiji
supporting information, p. 16010 - 16013 (2013/11/19)
The synthetic utility of quinone imine ketals in the context of asymmetric catalysis was disclosed for the first time. By expanding the utility of chiral Bronsted acid catalysis to the electrophilic activation of quinone imine ketals, we succeeded in the development of highly enantioselective arylation of encarbamates to give α-amino-β-aryl ethers wherein quinone imine ketals act as functionalized aromatic ring surrogate. Further transformations of the products were also examined to establish procedures to provide chiral β-aryl amines and α-aryl esters.
The Diels-Alder reactions of quinone imine ketals
Banfield, Scott C.,Kerr, Michael A.
, p. 131 - 138 (2007/10/03)
N-Benzoyl- and N-arylsulfonyl-p-benzoquinone-mono-imine ketals (QIKs) undergo smooth Diels-Alder cycloadditions with typical 1,3-butadienes to yield the expected endo adducts. Treatment with catalytic acid rapidly converts the adducts to dihydronaphthalen
Preparation of quinone-imide ketals from amides with hypervalent organo-iodine compounds
Barret,Daudon
, p. 2133 - 2134 (2007/10/02)
Iodosylbenzene in methanol in the presence of molecular sieves oxidises amides into quinone-imide mono ketals.
