87682-48-2Relevant academic research and scientific papers
Piers′ Borane-Induced Tetramerization of Arylacetylenes
Averdunk, Arthur,Becker, Jonathan,Gellrich, Urs,Hasenbeck, Max,Müller, Tizian
supporting information, (2022/01/04)
We herein report that the reaction of Piers′ borane, i. e. HB(C6F5)2, with an excess of arylacetylenes at room temperature leads to tetramerization of the acetylene and the diastereoselective formation of boryl-substituted
Cyano-Schmittel Cyclization through Base-Induced Propargyl-Allenyl Isomerization: Highly Modular Synthesis of Pyridine-Fused Aromatic Derivatives
You, Xu,Xie, Xin,Chen, Haoyi,Li, Yuxue,Liu, Yuanhong
supporting information, p. 18699 - 18705 (2016/01/25)
The cyano-Schmittel cyclization of i situ-generated cyano-allenes has been carried out. The DFT calculation results suggest that the diradical pathway plays a major role in this cyclization. The reactions can be conveniently performed in a one-pot manner through cascade Sonogashira coupling of terminal cyano-ynes with organic halides, followed by base-promoted propargyl-allenyl isomerization/cyclization, leading to an efficient access to pyridine-fused polycyclic architectures. In particular, a large variety of aryl or heteroaryl rings such as furans, thiophenes and pyridines can be incorporated into the follow-up cyano-Diels-Alder reactions, highlighting the great synthetic utility of this chemistry.
Competitive 1,2- and 1,5-hydrogen shifts following 2-vinylbiphenyl photocyclization
Lewis, Frederick D.,Sajimon, Meledathu C.,Zuo, Xiaobing,Rubin, Michael,Gevorgyan, Vladimir
, p. 10447 - 10452 (2007/10/03)
The photocyclization of 2-vinylbiphenyl and its derivatives has been proposed to occur via a two-step mechanism: photocyclization to form an unstable 8a,9-dihydro-phenanthrene intermediate, followed by exothermic unimolecular isomerization to a 9,10-dihyd
Anomaly in Palladium-Catalyzed Phenylethynylation of 2,2'-Dihalobiphenyls: Formation of Alkylidenefluorenes
Dougherty, T. Kirk,Lau, Kreisler S. Y.,Hedberg, Frederick L.
, p. 5273 - 5280 (2007/10/02)
2,2'-Diiodobiphenyl and 5,5'-dinitro-2,2'-dihalobiphenyls underwent palladium-catalyzed phenylethynylation with 2 mol of phenylacetylene to yield 3-(fluoren-9-ylidene)-1,3-diphenylpropyne and 3-(3,6-dinitrofluoren-9-ylidene)-1,3-diphenylpropyne, respectively.These fluorenyl compounds exhibited well-defined splitting patterns for the fluorenyl ring protons in the 250-MHz proton NMR spectra.The structure of 3-(fluoren-9-ylidene)-1,3-diphenylpropyne was further confirmed by an independent synthesis via the thermolysis of diethyl 3-(fluoren-9-ylidene)-1,3-diphenylpropen-1-yl phosphate.The mechanistic importance of the complex iodo(fluoren-9-ylidenebenzyl)bis(triphenylphosphine)palladium(II) in the catalytic cycle was established on the basis of its reaction with phenylacetylene to give 3-(fluoren-9-ylidene)-1,3-diphenylpropyne.
