- Synthesis of substituted indene derivatives via silver-catalyzed annulative 1:1 coupling of secondary benzyl alcohols with alkynes
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The annulative coupling of secondary benzyl alcohols with internal alkynes efficiently proceeds in the presence of a silver catalyst. The reaction gives 1,2,3-substituted indene derivatives selectively as 1:1 coupling products. The procedure provides a straightforward synthetic route to indenes from readily available starting materials upon treatment with a simple reaction system under mild conditions.
- Morisaka, Hideaki,Hirosawa, Keishi,Inai, Yasuhito,Usuki, Yoshinosuke,Satoh, Tetsuya
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supporting information
p. 456 - 458
(2021/03/16)
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- KHMDS mediated synthesis of 9-arylfluorenes from dibenzothiophene dioxides and arylacetonitriles by tandem SNAr-decyanation-based arylation
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A straightforward KHMDS mediated synthetic route to 9-arylfluorenes from readily available starting materials has been developed. This reaction involves SNAr reactions of dioxide with arylacetonitriles, followed by decyanation reaction. The pro
- Mylavarapu, Saketh,Yadav, Mamta,Bhanuchandra
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supporting information
p. 7815 - 7819
(2018/11/21)
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- Synthesis of multisubstituted indenes via iron-catalyzed domino reaction of benzylic compounds and alkynes
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A novel approach to synthesizing multisubstituted indenes by iron-catalyzed domino reaction of benzylic compounds and alkynes under mild conditions was developed. This system could be applied to various available substrates in a one-step synthetic procedure in moderate to good yields. Georg Thieme Verlag Stuttgart · New York.
- Chen, Yongxin,Li, Kangning,Liu, Xiang,Zhu, Jiaoyan,Chen, Baohua
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supporting information
p. 130 - 134
(2013/02/25)
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- Synthesis of substituted indenes through iron-catalyzed annulation of benzylic alcohols with alkynes
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A convenient and efficient method for the synthesis of polysubstituted indenes has been developed by the iron(III) trichloride-catalyzed tandem mono- and dibenzylation/cyclization reactions of benzylic alcohols with alkynes. This method is featured with the easily available starting materials, cheap catalyst, simple manipulation and mild conditions. Copyright
- Bu, Xiuli,Hong, Jianquan,Zhou, Xigeng
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supporting information; scheme or table
p. 2111 - 2118
(2011/10/09)
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- An efficient and general iron-catalyzed C-C bond activation with 1,3-dicarbonyl units as a leaving groups
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(Chemical Equation Presented) With our compliments: The 1,3-dicarbonyl unit has been shown to be a new and useful leaving group for iron-catalyzed bond cleavage (see scheme). This new strategy can complement the traditional Friedel-Crafts reaction and was applied in the synthesis of indene derivatives.
- Li, Huanrong,Li, Wenjuan,Liu, Weiping,He, Zhiheng,Li, Zhiping
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supporting information; experimental part
p. 2975 - 2978
(2011/05/05)
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- Catalytic regioselective synthesis of structurally diverse indene derivatives from N-benzylic sulfonamides and disubstituted alkynes
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An unprecedented protocol has been developed for the regioselective synthesis of structurally diverse indene derivatives from readily accessible N-benzylic sulfonamides and disubstituted alkynes through FeCl 3-catalyzed cleavage of sp3 carbon-nitrogen bonds to generate benzyl cation intermediates. In the presence of 10 mol % of FeCl 3, a broad range of N-benzylic sulfonamides smoothly react with internal alkynes, alkynylcarbonyl compounds, alkynyl chalcogenides, or alkynyl halides to afford various functionalized indene derivatives with extremely high regioselectivity.
- Liu, Cong-Rong,Yang, Fu-Lai,Jin, Yi-Zhou,Ma, Xian-Tao,Cheng, Dao-Juan,Li, Nan,Tian, Shi-Kai
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supporting information; experimental part
p. 3832 - 3835
(2010/11/17)
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- Au-catalyzed isomerization of cyclopropenes: a novel approach to indene derivatives
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AuPPh3Cl/AgOTf-catalyzed reaction of cyclopropenes is found to be highly efficient, giving indene derivatives in high yields. The reaction is suggested to proceed through gold vinyl carbenoid intermediate.
- Li, Changkun,Zeng, Yi,Wang, Jianbo
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supporting information; experimental part
p. 2956 - 2959
(2009/08/09)
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- (η5-triphenylindenyl)Ru(CO)2Cl: A new ruthenium catalyst for the highly efficient racemization of chiral 1-phenylethanol at room temperature
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A new ruthenium complex, (η5-triphenylindenyl)Ru(CO) 2Cl, was synthesized and successfully applied in the racemization of (S)-1-phenylethanol at room temperature. Instead of potassium tert-butoxide, stronger bases such as sodium hydr
- Xi, Qiang,Zhang, Weicheng,Zhang, Xumu
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p. 945 - 947
(2007/10/03)
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- Synthesis of diastereoisomeric 1,2,3-triphenylindans
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The stereoisomers of 1,2,3-triphenylindans were synthesized via 1,2,3-triphenylindan-1-ols. The configurational assignments of all the compounds were made by chemical and spectroscopic methods. An unexpected compound was isolated as a by-product of the Gr
- Alesso, Elba N.,Finkielsztein, Liliana M.,Lantano, Beatriz,Bianchi, Daniel E.,Moltrasio Iglesias, Graciela Y.,Aguirre, Jose M.
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p. 149 - 152
(2007/10/03)
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- Metal-catalyzed cyclopropene rearrangements for benzannulation: Evaluation of an anthraquinone synthesis pathway and reevaluation of the parallel approach via carbene-chromium complexes
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The reaction of 3-arylcyclopropenes with Cr(CO)6 and Mo(CO)6 produces naphthols, in an example of metal-promoted benzannulation. Substituents at C- 3 (in addition to aryl) have a strong effect on the success of the process: 3-H deriv
- Semmelhack,Ho, Suzzy,Cohen,Steigerwald,Lee,Lee,Gilbert, Adam M.,Wutff, William D.,Ball, Richard G.
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p. 7108 - 7122
(2007/10/02)
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- Decay of Electrogenerated Dianions of Acidic Indenes: an 'Indirect' Self-protonation Mechanism
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The electrode reduction of 1,2,3-triphenylindene, giving rise to the corresponding radical anion and dianion in two successive one-electron steps, was investigated in dimethylformamide with the aim of clarifying the role of the acidic substrate in the decay of electrogenerated bases.At - 50 deg C the direct protonation of the radical anion by indene (self-protonation) was too slow to be effective, and the proton transfer from indene to the dianion did appear kinetically unfavourable with respect to solution electron transfer between the same species (comproportionation).However, dianion protonation by an excess of water present in the solution can induce, through the action of OH- ions, the substrate to transform into its conjugate base.The effect resembles that predicted for a self-protonation mechanism and can be termed an 'indirect' self-protonation process.The proposed reaction scheme was confirmed by comparison of cyclic voltammetric responses with those derived by mathematical computation.The rate-constant values for the relevant steps, obtained by the fitting of experimental and computed data, are consistent with the corresponding values determined for similar compounds.
- Farnia, Giuseppe,Ludvik, Jiri,Sandona, Giancarlo,Severin, Maria Gabriella
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p. 1249 - 1254
(2007/10/02)
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- Formation of 2-Substituted 1,3-Diphenylindenes by an N-Bromosuccinimide Promted Dehydrocyclization of 2-Substituted 1,3,3-Triphenyl-1-propenes
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The reactions of a series of 2-substituted 1,3,3-triphenyl-1-propenes with N-bromosuccinimide (NBS) afforded the corresponding 2-substituted 1,3-diphenylindenes in moderate yields.A reaction mechanism involving a novel free-radical intramolecular ring-clo
- Yamamura, Kimiaki,Miyake, Hideyoshi,Sera, Akira
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p. 3699 - 3701
(2007/10/02)
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- A CONVENIENT SYNTHESIS OF 2-PHENYLINDENE
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A benzene solution of phenylacetic acid when passed over alumina at 420 deg C gave 2-phenylindene.
- Jayamani, M.,Pillai, C. N.
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p. 535 - 542
(2007/10/02)
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- The SRN1 Photoarylation of Indenyl Anions
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Irradiation of Me2SO solutions of indenyl anion and its phenylated analogues in the presence of bromobenzene produces the higher phenylated indenes.Thus indenyl anion (1b) yields 3-phenylindene (3a), 1-phenylindenyl anion (3b) yields 1,3- and 1,1-diphenylindene, 2-phenylindenyl anion (2b) produces 2,3-diphenylindene, 1,3-diphenylindenyl anion (6b) produces 1,1,3- and 1,2,3-triphenylindene, and 1,2-diphenylindenyl anion (5b) produces 1,2,3-triphenylindene (8).In liquid ammonia and tetrahydrofuran more complex reaction pathways are observed.The regiochemistry of phenylation is attributed to radical attack at the most basic site, in accord with a previously published model.
- Tolbert, Laren M.,Siddiqui, Shahabuddin
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p. 1744 - 1751
(2007/10/02)
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- CUMULENE PHOTOCHEMISTRY: PHENYL AND HYDROGEN MIGRATION IN PHENYLALLENE PHOTOREACTIONS
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Photoreactions of tetra- and triphenylallene and 1,3,3-triphenylcyclopropane in hydrocarbon solvents are reported.Intermediacy of vinylcarbenes is supported by independent generation experiments.
- Klett, Michael W.,Johnson, Richard P.
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p. 2523 - 2526
(2007/10/02)
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- REACTIONS FOLLOWING ELECTRON TRANSFER ORIGINS OF SELECTIVITY IN THE REACTION OF RADICALS WITH CARBANIONS
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The regiochemistry observed upon arylation of ambident carbanions by phenyl radicals can be readily explained by consideration of the site of greatest basicity.Thus 1,3-diphenylindenyl anion is arylated to give predominantly 1,1,3-triphenylindene despite the presumed greater stability of the intermediate leading to 1,2,3-triphenyl indene, that is, the 1,2,3-triphenylisoindene radical anion.This explanation may also account for the preference of C-alkylation rather than O-alkylation of nitrocarbanions and for the absence of O-arylation in the SRN1 arylation of enolates.The lack of reactivity of other carbanions is rationalized on thermodynamic grounds.
- Tolbert, Laren M.,Siddiqui, Shahabuddin
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p. 1079 - 1086
(2007/10/02)
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