121747-71-5Relevant academic research and scientific papers
Rhodium-Catalyzed Oxidative Benzannulation of N-Pivaloylanilines with Internal Alkynes through Dual C?H Bond Activation: Synthesis of Highly Substituted Naphthalenes
Zhang, Xuan,Yu, Xiaoqiang,Feng, Xiujuan,Yamamoto, Yoshinori,Almansour, Abdulrahman I.,Arumugam, Natarajan,Kumar, Raju Suresh,Bao, Ming
, p. 3241 - 3250 (2016)
An efficient method was developed for the synthesis of highly substituted naphthalenes through rhodium-catalyzed oxidative benzannulation of N-pivaloylanilines with internal alkynes. The benzannulation reaction proceeded smoothly through dual C?H bond act
Palladium catalyzed synthesis of highly substituted naphthalenes via direct ring construction from amides with alkynes
Wu, Junliang,Cui, Xiuling,Mi, Xia,Li, Ying,Wu, Yangjie
supporting information; experimental part, p. 6771 - 6773 (2010/11/03)
The direct ring construction of amides with alkynes catalyzed by palladium acetate with cheap oxidant under an air atmosphere has been realized. A variety of novel highly substituted naphthalenes 3a-3l have been prepared chemo- and regioselectively in 55-97% yields under mild conditions. Product 3j emits intense blue luminescence peaked at 435 nm with a good blue purity.
Reactivity of Cyclopalladated Compounds. Part 18. Compared Reactivity of the Pd-C Bonds of Two Closely Related Six-membered Palladocyclic Rings with Substituted Alkynes. X-Ray and Molecular Structures of (R = CO2Et) and (R = CO2Me>
Dupont, Jairton,Pfeffer, Michel,Daran, Jean-Claude,Gouteron, Jacqueline
, p. 2421 - 2430 (2007/10/02)
The reactions between alkynes and the chloride-bridged cyclopalladated dimers derived from orthopalladation of acetanilide, (1), and amidine, (2), afforded organometallic products in which one, two, or three alkynes had been inserted into the Pd-C bonds of (1) and (2), the ratio of alkyne:palladium in the final products being independent of the stoicheiometry of the reaction.Compound (1) gave with hexafluorobut-2-yne the mono-inserted product .With diphenylacetylene it gave an unstable product (7) in which two alkynes had been added per palladium atom forming with the acetanilide unit a spirocyclic ligand η3-bonded to the palladium centre.Compound (7) decomposed on heating to afford quantitatively the pentasubstituted naphthalene derivative C10H3Ph4(NHCMe=O).Compound (2) reacted with diphenylacetylene and ethyl 3-phenylpropionate to give the di-inserted products (11, R = Ph; 12, R = CO2Et).The structure of (12) was ascertained by an X-ray structure determination, which confirmed the regioselectivity of the insertion reaction and that (12) is an eight-membered palladocyclic ring through the co-ordination to the metal of the nitrogen atom immediately adjacent to the phenyl ring.Triple insertion of alkynes was observed when reacting (1) and (2) with dimethyl acetylenedicarboxylate affording (9, Y = O; 13, Y = NPh).The structure of (9) has been confirmed by an X-Ray diffraction study.A related triple insertion occured when treating (1) with but-2-yne affording a thermally unstable intermediate; its depalladation led to trans-o-C6H4NHCMe=O)CH=CH(C5Me5).
