A facile synthesis of 2-arylindenes by Pd-catalyzed direct arylation of indene with aryl iodides

Origin of the N-methyl and N-phenyl substituent effects on the fluorescence vibronic structures of trans-4-aminostilbene and its derivatives in hexane

“…Solvents for organic synthesis were reagent grade or HPLC grade (Aldrich, Merck, or Mallinckrodt), but all were HPLC grade for spectroscopy and quantum yield measurements. The syntheses of compounds 2x, 21 3x, 22 4b, 23 4x, 24 and 4y 25 have been reported previously, and the other compounds were prepared according to Schemes 1 and 2. The characterization data of these new compounds are as follows:…”

Facile Synthesis of 3-Arylindenes by HMPA-Promoted Direct Arylation of Indenes with Aryl Fluorides

“…In 2002, Nifant’ev et al reported a facile Pd-catalyzed direct arylation of indene with aryl iodides to afford a mixture of 2- and 3-arylindenes in a 4/1 ratio (Scheme 1a). 9 The conventional method for the preparation of 3-substituted indenes involves first formation of indenyl lithium, generated in situ by deprotonation of indene with n -butyl lithium and subsequently reaction with electrophiles (Scheme 1b–d). 10 This method suffers from several drawbacks, such as the use of very low temperatures, long reaction time, and unsatisfactory regioselectivity.…”

3,5-Bis(trifluoromethyl)iodobenzene

“…Arylations. The synthesis of 2-arylindenes though Pdcatalyzed direct arylation of indene with 3,5-bis(trifluoromethyl) iodobenzene has been reported by Nifant'ev et al 6 1-and 3-Arylindenes are normally the major products generated via a successive cis-addition of aryl-Pd-Hal and cis-elimination of H-Pd-Hal. 7 Nevertheless, 2-arylindenes can be synthesized in the presence of palladium acetate with more extensive heating than that required for the typical Heck reaction (eq 4).…”