2294-87-3Relevant articles and documents
Synthesis and characterization of 1- and 2-(ω-alken-1-yl)indenes, their lithium salts and dichlorozirconium(IV) complexes
Schumann, Herbert,Karasiak, Dirk F.,Muehle, Stefan H.,Halterman, Ronald L.,Kaminsky, Walter,Weingarten, Ulrich
, p. 356 - 372 (1999)
A series of new 1-, 2-, and multi-substituted indenes has been synthesized and characterized. The reaction of indenyl lithium or 4,7-dimethylindenyl lithium with alkenyl bromides yielded a mixture of 1- and 3-allylindene (1), 3-(3-buten-1-yl)indene (2), 3-(4-penten-1-yl)indene (3), 3-allyl-4,7-dimethylindene (4), 3-(3-buten-1-yl)-4,7-dimethylindene (5), as well as 3-(4-penten-1-yl)-4,7-dimethylindene (6). The 2-substituted indenes 2-allylindene (7), 2-(3-buten-1-yl)indene (8), 2-(4-penten-1-yl)indene (9), 2-allyl-4,7-dimethylindene (10), 2-(3-buten-1-yl)-4,7-dimethylindene (11), and 2-(4-penten-1-yl)-4,7-dimethylindene (12) were prepared by PdCl2(DPPF) or NiCl2(DPPE) catalyzed cross-coupling reactions of the appropriate Grignard reagents with 2-bromoindene or 2-bromo-4,7-dimethylindene. Alkenylation of 3-methylindenyl lithium and 2,4,7-trimethylindenyl lithium produced 1-(3-buten-1-yl)-3-methylindene (13) or 1-(3-buten-1-yl)-2,4,7-trimethylindene (14), respectively. The indene derivatives 1-14 react with n-butyl lithium in hexane yielding the corresponding lithium salts 1a-14a. Zirconium tetrachloride reacts with 1a, 2a, 4a-6a and 11a-14a under formation of the corresponding bis(indenyl)zirconium dichloride complexes 1b, 2b, 4b-6b and 11b-14b. All compounds were characterized by elemental analysis, 1H and 13C{1H}-NMR spectroscopy and mass spectrometry, 5b and 12b also by single crystal X-ray structural analysis. 1b, 4b-6b and 11b-13b are active catalysts for the polymerization of ethene and propene.
Gold- or Indium-Catalyzed Cross-Coupling of Bromoalkynes with Allylsilanes through a Concealed Rearrangement
De Orbe, M. Elena,Zanini, Margherita,Quinonero, Ophélie,Echavarren, Antonio M.
, p. 7817 - 7822 (2019/08/20)
The gold(I)-catalyzed reaction of bromoalkynes with allylsilanes gives 1,4-enynes in a formal cross-coupling reaction. Mechanistic studies revealed the involvement of gold(I) vinylidenes or vinylidenephenonium gold(I) cations depending on the substituent on the bromoalkyne. In the case of bromo arylalkynes, the vinylidenephenonium gold(I) cations lead to 1,4-enynes via a 1,2-aryl rearrangement. The same reactivity has been observed in the presence of InBr3
Towards benign synthesis of indenes from indanones: Zinc-mediated allylation of ketones in aqueous media as a source of substituted indenyl ligand precursors
Silver, Satu,Leppaenen, Ann-Sofie,Sjoeholm, Rainer,Penninkangas, Antti,Leino, Reko
, p. 1058 - 1081 (2007/10/03)
Substituted indenes are valuable ligand precursors for transition-metal complexes. Previously, most of the methods employed for the preparation of alkyl-substituted indenes have involved the use of air-sensitive organometallic lithium or Grignard reagents
