32377-13-2

Usage

InChI:InChI=1/C20H16O/c1-21-15-8-6-7-14(13-15)20-18-11-4-2-9-16(18)17-10-3-5-12-19(17)20/h2-13,20H,1H3

Upstream product

• 486-25-9 9-fluorenone 
• 2398-37-0 3-methoxyphenyl bromide 
• 881-04-9 9H-fluoren-9-yllithium 
• 86-73-7 9H-fluorene 
• 2845-89-8 1-chloro-3-methoxy-benzene 
• 459-60-9 1-fluoro-4-methoxybenzene 
• 36282-40-3 (3-methoxyphenyl)magnesium bromide 
• 57028-29-2 9-(3-methoxyphenyl)fluoren-9-ol 
• 78229-10-4 9-(3-Methoxy-phenyl)-9-phenyl-9H-fluorene 

Relevant academic research and scientific papers

LDA-Mediated Synthesis of Triarylmethanes by Arylation of Diarylmethanes with Fluoroarenes at Room Temperature

A practical and convenient approach for the secondary C(sp3)-H arylation of diarylmethanes with various fluoroarenes is described. The reaction proceeds smoothly in the presence of LDA (lithium diisopropylamide) at room temperature and affords triarylmethanes in moderate to high yields.

Direct C-H bond arylation of fluorenes with aryl chlorides catalyzed by N-heterocyclic carbene-palladium(ii)-1-methylimidazole complex and further transformation of the products in a one-pot procedure

We report here the NHC-Pd(ii)-Im complex 1-catalyzed direct C-H bond functionalization of the C9 position of fluorenes with aryl chlorides and further transformation of the resulting products in a one-pot procedure. Under the optimal conditions, arylated fluorenes can be obtained in moderate to almost quantitative yields using various activated and unactivated (hetero)aryl chlorides as the arylating reagents. Furthermore, if the mixture from the arylation reaction is exposed to air, the C9-oxidized products can be obtained in acceptable to good yields in a one-pot procedure. In addition, alkyl groups can also be efficiently introduced to the above mixture from the arylation reaction, producing further C9-alkylated products in good to almost quantitative yields in a one-pot procedure, thus providing an expedient, inexpensive and practical strategy for the mono- and di-functionalization of fluorenes. This journal is

Palladium-catalysed direct cross-coupling of secondary alkyllithium reagents

Palladium-catalysed cross-coupling of secondary C(sp3) organometallic reagents has been a long-standing challenge in organic synthesis, due to the problems associated with undesired isomerisation or the formation of reduction products. Based on our recently developed catalytic C-C bond formation with organolithium reagents, herein we present a Pd-catalysed cross-coupling of secondary alkyllithium reagents with aryl and alkenyl bromides. The reaction proceeds at room temperature and on short timescales with high selectivity and yields. This methodology is also applicable to hindered aryl bromides, which are a major challenge in the field of metal catalysed cross-coupling reactions.

Flash photolysis study of a Friedel-Crafts alkylation. Reaction of the photogenerated 9-fluorenyl cation with aromatic compounds

A combination of flash photolysis and product analysis is employed to investigate the reaction of aromatic compounds (ArH) with the 9-fluorenyl cation (Fl+) photogenerated from 9-fluorenol in 1,1,1,3,3,3-hexafluoroisopropyl alcohol (HFIP).The availability of the photochemical route to Fl+ means that the reaction of benzylic-type cation with ArH can be directly followed by flash photolysis.An additional feature with electron-rich ArH is that the cyclohexadienyl cation is observed to grow as Fl+ decays.Thus both cationic intermediates of a Friedel-Crafts alkylation are observed in the same experiment.The formation of the cyclohexadienyl cation is demonstrated to be reversible, or at least quasi-reversible, with the kinetic analysis furnishing absolute rate constants for the formation of this cation as well as for its loss of H+ and Fl+.Values of kH:kD for benzene:benzene and toluene:toluene are ca. 1.5 and demonstrate that Fl+ addition is at least partly reversible with these compounds as well.The Hammett ρ+ value obtained for a series of the less electron-rich ArH is -8, indicative of a transition state with considerable cyclohexadienyl cation character.Anisole shows a negative deviation from from Hammett correlation line, explained by the addition of Fl+ to ArH becoming encounter-controlled.This behaviour is dramatically illustrated in a comparison of data for Fl+ and Br2.For the less electron-rich ArH, rate constants for the two electrophiles are parallel.However, from m-xylene through pentamethylbenzene, the rate with Fl+ is unchanged, while the rate with Br2 increases over 1000-fold.The concept of encounter control with Fl+ is strongly supported by the absolute rate constants, which for the electron-rich ArH are all in the range 1-2 E9 dm3 mol-1 s-1, a magnitude typical of diffusion-controlled reactions.The electron-rich ArH also show no intermolecular selectivity since their reactions are encounter-controlled, but have a high intramolecular selectivity.It is suggested that a factor influencing the latter is the reversibility of formation of the cyclohexadienyl cation from the encounter complex.

Reductive Cleavage of 9,9-Diarylfluorenes by Potassium in 1,2-Dimethoxyethane

Reduction of 9,9-diarylfluorenes by potassium in 1,2-dimethoxyethane results in cleavage of one of the aryl rings to form 9-arylfluorenyl anions.Product analyses and kinetic studies indicate that cleavage occurs via dianions, produced by disproportionation of the initially formed radical anions.