5324-00-5Relevant articles and documents
The Synthesis of Benzofulvenes through Palladium-Catalyzed Sequential Three-Component Reactions
Zhou, Bo,Wu, Zhuo,Qi, Weixin,Sun, Xueliang,Zhang, Yanghui
, p. 4480 - 4484 (2018/10/31)
An approach for the synthesis of benzofulvenes has been developed through palladium-catalyzed sequential three-component reactions. The reactions likely involve C,C-palladacycles as the key intermediates. The palladacycles are generated through cascade reactions of aryl halides and alkynes, and then reacted with CH2Br2 to form benzofulvenes as the final products. (Figure presented.).
Intramolecular addition of triarylmethanes to alkynes promoted by KOtBu/DMF: A synthetic approach to indene derivatives
Chen, Yan-Yan,Chen, Zhen-Yu,Zhang, Niu-Niu,Chen, Jia-Hua,Zhang, Xue-Jing,Yan, Ming
, p. 599 - 606 (2016/02/19)
A method for the intramolecular addition of triarylmethanes to alkynes has been developed. The reaction was efficiently promoted by KOtBu/DMF without any transition-metal catalyst. A variety of indene derivatives were prepared in moderate to good yields. A cascade cyclization of 2-alkyl-substituted substrates at elevated reaction temperature gave bicyclic indene derivatives. The reaction is proposed to proceed through the generation of a triphenylmethyl radical. Indene derivatives were prepared by the intramolecular addition of triarylmethanes to alkynes promoted by KOtBu/DMF. A cascade cyclization of 2-alkyl-substituted substrates at elevated reaction temperature gave bicyclic indene derivatives. A free-radical reaction mechanism is proposed.
Synthesis of 2-bromo-1-aryl-1H-indenes via a Ag(I) promoted domino 2π-electrocyclic ring-opening/4π-electrocyclization reaction of 1,2-diaryl substituted gem-dibromocyclopropanes
Rosocha, Gregory,Batey, Robert A.
, p. 8758 - 8768 (2013/09/23)
2-Bromo-1-aryl substituted indenes can be synthesized from 1,2-diaryl substituted gem-dibromocyclopropanes via a domino reaction sequence. The cascade reaction involves silver(I) promoted ionization and 2π-disrotatory electrocyclic ring-opening, followed by a 4π-conrotatory electrocyclic ring closing reaction of the allylic carbocation intermediate. Reaction conditions utilize silver tetrafluoroborate (AgBF4) in dichloroethane at 65 C. Selectivity effects for the electrocyclization were also studied. The 2-bromoindenes can be further functionalized using cross-coupling reactions, such as the Suzuki-Miyaura protocol. The alkene π-bond of the indenes can also be isomerized to give the thermodynamically more stable 2-bromo-3-aryl-1H-indene isomers using triethylamine in dichloromethane at room temperature.
