89215-37-2Relevant academic research and scientific papers
Access to chiral tetrahydrofluorenes through a palladium-catalyzed enantioselective tandem intramolecular Heck/Tsuji-Trost reaction
Zhang, Ying,Shen, Hong-Cheng,Li, Yang-Yang,Huang, Yong-Shuang,Han, Zhi-Yong,Wu, Xiang
supporting information, p. 3769 - 3772 (2019/04/01)
A palladium-catalyzed enantioselective coupling of 2,5-cyclohexadienyl-substituted aryl iodides and carbon or heteroatom nucleophiles is described. The reaction proceeded via a tandem asymmetric Heck insertion and Tsuji-Trost allylation, enabling the rapi
Palladium-catalyzed cross-coupling of 2,5-cyclohexadienyl-substituted aryl or vinylic iodides and carbon or heteroatom nucleophiles
Larock, Richard C.,Han, Xiaojun
, p. 1875 - 1887 (2007/10/03)
2,5-Cyclohexadienyl-substituted aryl or vinylic iodides have been reacted with carbon nucleophiles (diethyl malonate and 2-methyl-1,3- cyclohexanedione), nitrogen nucleophiles (morpholine, potassium phthalimide, N-benzyl tosylamide, di-tert-butyl iminodicarboxylate, lithium azide, and anilines), a sulfur nucleophile (sodium benzenesulfinate), and oxygen nucleophiles (lithium acetate and phenols) to afford products of cyclization and subsequent cross-coupling in good to excellent yields. In most cases, this process is highly diastereoselective. The reaction is believed to proceed via (1) oxidative addition of the aryl or vinylic iodide to Pd(0), (2) organopalladium addition to one of the carbon-carbon double bonds, (3) palladium migration along the carbon chain on the same face of the ring to form a π-allylpalladium intermediate, and (4) nucleophilic displacement of the palladium.
