837365-66-9Relevant academic research and scientific papers
Palladium-catalyzed oxidative diarylating carbocyclization of enynes
Jiang, Min,Jiang, Tuo,B?ckvall, Jan-E.
, p. 3538 - 3541 (2012)
A mild and efficient palladium-catalyzed oxidative diarylating carbocyclization of enynes is described. The reaction tolerates a range of functionalized arylboronic acids to give diarylated products in good yields. Control experiments suggest that the reaction starts with an arylpalladation of the alkyne, followed by carbocyclization, transmetalation, and reductive elimination to afford the diarylated product.
Enantioselective rhodium-catalyzed cycloisomerization of (E)-1,6-enynes
Deng, Xu,Ni, Shao-Fei,Han, Zheng-Yu,Guan, Yu-Qing,Lv, Hui,Dang, Li,Zhang, Xu-Mu
supporting information, p. 6295 - 6299 (2016/05/24)
An enantioselective rhodium(I)-catalyzed cycloisomerization reaction of challenging (E)-1,6-enynes is reported. This novel process enables (E)-1,6-enynes with a wide range of functionalities, including nitrogen-, oxygen-, and carbon-tethered (E)-1,6-enynes, to undergo cycloisomerization with excellent enantioselectivity, in a high-yielding and operationally simple manner. Moreover, this RhI-diphosphane catalytic system also exhibited superior reactivity and enantioselectivity for (Z)-1,6-enynes. A rationale for the striking reactivity difference between (E)- and (Z)-1,6-enynes using RhI-BINAP and RhI-TangPhos is outlined using DFT studies to provide the necessary insight for the design of new catalyst systems and the application to synthesis. A solution after 15 years: The first rhodium(I)-catalyzed asymmetric cycloisomerization reaction of challenging (E)-configured 1,6-enyes is reported. The reaction provides access to five-membered carbo- and heterocycles with excellent enantioselectivity. DFT studies provide a rationale for the striking reactivity difference between (E)- and (Z)-1,6-enynes using RhI-BINAP and RhI-TangPhos.
