14213-80-0Relevant articles and documents
A rhodium(I)-catalysed formal intramolecular C-C/C-H bond metathesis
Matsuda, Takanori,Yuihara, Itaru
supporting information, p. 7393 - 7396 (2015/04/27)
Phenylcyclobutanes underwent skeletal reorganisation in the presence of Wilkinson's catalyst to afford indanes through a cascade process involving chelation-assisted C-C bond cleavage and intramolecular C-H bond cleavage.
Fritsch-Buttenberg-Wiechell rearrangement to alkynes from gem-dihaloalkenes with lanthanum metal
Umeda, Rui,Yuasa, Takumi,Anahara, Namika,Nishiyama, Yutaka
supporting information; experimental part, p. 1916 - 1919 (2011/05/14)
The first example of the FBW rearrangement using of lanthanum metal and a catalytic amount of iodine was disclosed. When gem-diiodo- and gem-dibromoalkenes were treated with lanthanum metal in the presence of a catalytic amount of iodine, the reductive dehalogenation of these compounds smoothly proceeded to produce the corresponding alkynes in moderate to good yields.
Ligandless iron-catalyzed desulfinylative C-C allylation reactions using Grignard reagents and alk-2-enesulfonyl chlorides
Volla, Chandra M. R.,Markovic, Dean,Dubbaka, Srinivas Reddy,Vogel, Pierre
experimental part, p. 6281 - 6288 (2011/02/28)
Alk-2-enesulfonyl chlorides 1-4 were synthesized by the BCl3-promoted ene reaction of alkenes with SO2. These sulfonyl chlorides were then used as electrophilic partners in iron-catalyzed desulfinylative cross-coupling reactions with different Grignard reagents (aromatic, aliphatic, and heteroaromatic). The reaction can be catalyzed with even 2 mol-% of the simple iron salt Fe(acac)3. The regioselectivity of these allylations was studied by using sulfonyl chlorides 3 and 4 with aryl Grignard reagents. The scope of these allylations was further extended by the coupling of ester-substituted alk-2-enesulfonyl chloride 10 with aromatic Grignard reagents. Symmetrical products were synthesized by double C-C allylation with the use of 2-methylidenepropane-1,3-disulfonyl chloride (12). Wiley-VCH Verlag GmbH & Co. KGaA.
Modern Friedel-Crafts chemistry. Part-26. A facile synthesis of trans-2-methyl-1-phenylindan via rearranged intramolecular cyclialkylation of 1,2-diphenyl-2-methyl-2-propanol under Friedel-Crafts conditions
Khalaf, Ali A.,Albar, Hassan A.
, p. 518 - 521 (2007/10/03)
1,2-Diphenyl-2-methyl-2-propanol (1) was prepared by two alternative Grignard methods. Treatment of 1 with AlCl3, AlCl3/CH 3NO2 or K10 clay catalyst in benzene, toluene of dichloromethane solvent at varying temperatures for varying times gave trans-2-methyl-1-phenylindan (4) as sole or major product. Side products including isomeric alkenes 7 and 8, isomeric chlorides 9 and 10, isomeric triarylated isobutanes 11-14, 1-methyl-3-phenylindan (5) and 2-methyl-1-phenylindene (6) were also detected by GC-MS technique. Mechanistic interpretations and explanatory comments are offered.
Suzuki-Miyaura and related cross-couplings in aqueous solvents catalyzed by di(2-pyridyl)methylamine-palladium dichloride complexes
Najera, Carmen,Gil-Molto, Juan,Karlstroem, Sofia
, p. 1798 - 1811 (2007/10/03)
Di(2-pyridyl)methylamine-based palladium dichloride complexes 4 are versatile catalysts for different types of cross-coupling reactions in water or aqueous solvents under aerobic conditions. The Suzuki-Miyaura reaction of arylboronic acids can be performed with bromoarenes under water reflux using K2CO3 as base or at room temperature or 60°C in aqueous methanol using KOH as base. For aryl chlorides the corresponding cross-couplings with arylboronic acids can be carried out in refluxing water with K2CO3 as base and TBAB as additive to provide biaryls and heterobiaryls. Arylboronic acids react with benzylic chlorides and allylic substrates such as chlorides, acetates or carbonates also in refluxing water with K2CO3 as base or at room temperature in aqueous acetone and KOH as base, to give diarylmethanes and arylpropenes. Trimethylboroxine and alkylboronic acids are coupled with bromo- and chloroarenes under water at reflux with K2CO3 as base and TBAB as additive to furnish methyl- and butylarenes. These cross-couplings have also been performed in shorter times under microwave irradiation. Several important intermediates such as, 4′-methylbiphenyl-2-carbonitrile, 4-biphenylacetic acid, 3-(3-methylphenyl)benzoic acid, 4,5-diphenyl-2-methyl- 3(2H)pyridazinone and 2-(4′-fluorobenzyl)thiophene have been prepared under aqueous and aerobic conditions in good yields.
The Olefin Synthesis from β-Hydroxyalkylphosphonates Induced by Fluorides or Relatively Weak Bases
Kawashima, Takayuki,Ishii, Takafumi,Inamoto, Naoki,Tokitoh, Norihiro,Okazaki, Renji
, p. 209 - 219 (2007/10/03)
β-Hydroxyalkylphosphonates, which were prepared readily from alkylphosphonates and carbonyl compounds, were treated with a fluoride ion such as CsF or with relatively weak bases such as K2CO3 in N,N-dimethylformamide to give the corresponding olefins in good yields. One molar equivalent of water to bases is effective for increasing the yields of olefins. The stereochemistry of erythro-dimethyl (2-hydroxy-1-methyl-2-phenyl)ethylphosphonate was determined by X-ray crystallographic analysis. Use of threo-isomer gave (E)-olefin exclusively, while that of erythro-enricned isomer afforded predominantly (Z)-olefin, indicating that the present olefination proceeds stereospecifically in a manner of syn-elimination.
Synthesis, structural characterization, and reactivity of zirconium complexes containing trimethylenemethane-based ligands
Rodriguez, George,Bazan, Guillermo C.
, p. 343 - 352 (2007/10/03)
General synthetic routes to zirconium metallocene-like complexes containing derivatives of the dianionic trimethylenemethane (TMM) ligand are presented. One approach consists of reacting the dilithium salts of TMM, tribenzylidenemethane (TBM), tert-butylt
Chelation assistance in the activation of Csp3-S bonds in nickel-catalyzed cross-coupling reactions
Wong, Ken-Tsung,Yuan, Tien-Min,Wang, Maw Cherng,Tung, Hsiao-Hsian,Luh, Tien-Yau
, p. 8920 - 8929 (2007/10/02)
An unprecedented chelation approach to activate Csp3-S bonds in nickel-catalyzed cross-coupling reactions is described. Our theme was based on the formation of a chelation complex which results in the enhancement of the reactivity of aliphatic
Synthesis and Thermolysis of Tetracoordinate 1,2-Oxaphosphetanes Stabilized by Steric Protection
Kawashiwa, Takayuki,Takami, Hiromishi,Okazaki, Renji
, p. 1487 - 1490 (2007/10/02)
The title compounds bearing a 2,4,6-triisopropylphenyl group stable in air at room temperature were synthesized in good yields by intramolecular dehydration of the corresponding β-hydroxy phosphinic acids.Thermolysis gave the corresponding olefin along wi
Intramolecular Dehydration of β-Hydroxyalkylphosphonic Acid Monoesters. A Novel Type of Olefin Formation
Kawashima, Takayuki,Nakamura, Mio,Nakajo, Akira,Inamoto, Naoki
, p. 1483 - 1486 (2007/10/02)
The title reaction using dicyclohexylcarbodiimide (DCC) gave stereospecifically the corresponding olefins in good yields via tetracoordinate 1,2-oxaphosphetanes.Use of more than one equivalent of DCC afforded better yields of the olefin.
