37051-70-0Relevant articles and documents
Oxidative Catalytic Spiroketalization Leading to Diastereoselective Synthesis of Spiro[benzofuran-2,1′-isochromene]s
Qiu, Jiang-Kai,Hao, Wen-Juan,Li, Guigen,Jiang, Bo
, p. 1182 - 1192 (2018)
A new one-pot, two-step silver-catalyzed spiroketalization of the in-situ generated quinone imine ketals (QIKs) with β-alkynyl ketones has been established, enabling multiple C?O and C?C bond-forming reactions to access densely functionalized spiro[benzof
Highly enantioselective [3+2] coupling of indoles with quinone monoimines promoted by a chiral phosphoric acid
Liao, Lihua,Shu, Chang,Zhang, Minmin,Liao, Yijun,Hu, Xiaoyan,Zhang, Yonghong,Wu, Zhijun,Yuan, Weicheng,Zhang, Xiaomei
, p. 10471 - 10475 (2014)
Highly enantioselective [3+2] coupling of 3-substituted indoles with quinone monoimines promoted by a chiral phosphoric acid has been reported. A large variety of benzofuroindolines were prepared in moderate to good yields (up to 98 %) with generally excellent enantioselectivities (up to 99 % ee). Benzofuroindolines: The title reaction has been realized. A wide variety of benzofuroindolines have been prepared with moderate to good yields in moderate to excellent enantioselectivities. Ts=4-toluenesulfonyl.
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
, 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.).
Dehydrogenation/(3+2) Cycloaddition of Saturated Aza-Heterocycles via Merging Organic Photoredox and Lewis Acid Catalysis
Xiao, Teng-Fei,Zhang, Yi-Fan,Hou, Wen-Tao,Yan, Pen-Ji,Hai, Jun,Xu, Peng-Fei,Xu, Guo-Qiang
supporting information, p. 8942 - 8946 (2021/11/24)
Herein, we report a photoinduced dehydrogenation/(3+2) cycloaddition reaction by merging organic photoredox and Lewis acid catalysis, providing a straightforward and efficient approach for directly installing a benzofuran skeleton on the saturated aza-heterocycles. In this protocol, we also describe a novel organic photocatalyst (t-Bu-DCQ) with the advantages of a wider redox potential, easy synthesis, and a low price. Furthermore, the stepwise activation mechanism of dual C(sp3)-H bonds was demonstrated by a series of experimental and computational studies.