Synthesis and Characterization of Intramolecularly Stabilized Chiral Dimethylindium Alkoxides and their Use as Cross Coupling ReagentsProfessor Joachim Strähle zum 65. Geburtstag gewidmet

Schumann, Herbert; Kaufmann, Jens; Wassermann, Birgit C.; Girgsdies, Frank; Jaber, Nimer; Blum, Jochanan

doi:10.1002/1521-3749(200206)628:5<971::aid-zaac971>3.0.co;2-g

Cited by 19 publications

(10 citation statements)

References 14 publications

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“…The emergence of indium as an important Lewis acid catalyst and the relative paucity of indium complexes supported by chiral ligands ,− emphasize the importance of developing well-characterized chiral indium complexes. − In this work, we present our investigations into the coordination chemistry and structural characteristics of a family of indium(III) complexes supported by a chiral tridentate diaminophenol ligand, H(NN H O), and provide explanations for the significant halide effect observed in these systems.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structural Studies of Chiral Indium(III) Complexes Supported by Tridentate Diaminophenol Ligands

Acosta-Ramírez

Douglas

et al. 2010

Inorg. Chem.

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Indium(III) dimethyl, dihalide, and alkoxy-bridged complexes bearing a chiral diaminophenoxy tridentate ligand [NN(H)O](-) were synthesized. The dimethyl complex (NN(H)O)InMe(2) (1) was unreactive toward ethanol and 2-propanol and only partially reactive toward the more acidic phenol. The dihalide complexes (NN(H)O)InX(2) (X = Cl (3), Br (4), I (5)) reacted with NaOEt to form robust alkoxy-bridged complexes with the formula {[(NN(H)O)InX](2)(mu-X)(mu-OEt)} (X = Cl (6), Br (7), I (8)). The reaction of the alkoxy-bridged complexes with water produced hydroxy-bridged dinuclear indium compounds. The hydroxy-bridged complex bearing a chloride ligand [(NN(H)O)InCl(mu-OH)](2) (9) was significantly more reactive toward dissociation and formation of a pyridine adduct than the iodo analogue [(NN(H)O)InI(mu-OH)](2) (10). All compounds were fully characterized in solution by NMR spectroscopy and in the solid state by single-crystal X-ray diffraction. In addition, DFT calculations were used to help explain the reactivity trends observed.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Structural Studies of Chiral Indium(III) Complexes Supported by Tridentate Diaminophenol Ligands

Acosta-Ramírez

Douglas

et al. 2010

Inorg. Chem.

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“…In summary, we have demonstrated that the intramolecularly stabilized indium (III) compounds 3 and 4, which are readily prepared from trimethyl indium, 7 are highly useful reagents for the Pd-catalyzed cross-methylation of chloroarene-Cr(CO) 3 complexes. The developed procedure is characterized by high yields of products and operational simplicity.…”

Section: Methodsmentioning

confidence: 94%

“…In recent years, indium (III) organometallic compounds have demonstrated their great potential in transition-metal (Pd or Ni) catalyzed cross-coupling chemistry. [6][7][8][9][10][11][12] Besides their high reactivity such reagents exhibit a good functional group compatibility, a low toxicity and ease of handling.…”

Section: Methodsmentioning

confidence: 99%

Pd-Catalyzed Cross-Coupling of Chloroarene-Cr(CO)3 Complexes with Stabilized Organoindium(III) Reagents Under Remarkably Mild Conditions

Gotov¹,

Kaufmann²,

Schumann³

et al. 2002

Synlett

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The palladium catalyzed cross-methylation of intramolecularly stabilized dimethylindium (III) compounds (3 and 4) with different chloroarene-Cr(CO) 3 complexes have been studied. Under mild conditions (40 °C in THF, 3 h) high yields (up to 96%) of the coupling products were obtained in the presence of 1-10 mol% of PdCl 2 (PPh 3 ) 2 . With MeMgCl almost no conversion was observed under the same conditions.

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“…Diminishing copper content in the human body may result in many kinds of diseases, including sugar diabetes, cardiovascular diseases, and so on [2]. Schumann et al [3] synthesized a novel complex which consisted of trimethylindium and (1R,2S)-2-(dimethylamino)-1-phenylpropanol used as a preferable cross-coupling reagent. Nöth et al [4] synthesized a novel complex of (1R,2S)-2-(dimethylamino)-1-phenylpropanol with AlH 3 ÁNMe 3 used as a hydride reduction reagent, which may show very high enantioselectivity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structure and standard molar enthalpy of formation of bis(trans-bis(N,N-dimethyl-(1-(R)-phenyl-2-(S)-methyl-2-aminoethoxy-N,O))-copper(II)) heptahydrate

Dan

Chen²,

et al. 2011

The Journal of Chemical Thermodynamics

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Synthesis and Characterization of Intramolecularly Stabilized Chiral Dimethylindium Alkoxides and their Use as Cross Coupling ReagentsProfessor Joachim Strähle zum 65. Geburtstag gewidmet

Cited by 19 publications

References 14 publications

Synthesis and Structural Studies of Chiral Indium(III) Complexes Supported by Tridentate Diaminophenol Ligands

Synthesis and Structural Studies of Chiral Indium(III) Complexes Supported by Tridentate Diaminophenol Ligands

Pd-Catalyzed Cross-Coupling of Chloroarene-Cr(CO)3 Complexes with Stabilized Organoindium(III) Reagents Under Remarkably Mild Conditions

Synthesis, crystal structure and standard molar enthalpy of formation of bis(trans-bis(N,N-dimethyl-(1-(R)-phenyl-2-(S)-methyl-2-aminoethoxy-N,O))-copper(II)) heptahydrate

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