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Metal iridium complex, monocrystal, benzoindole compound, and synthesis method and applications thereof

A technology of metal iridium and complexes, applied in the field of metal iridium complexes, can solve problems such as no literature reports

Active Publication Date: 2017-01-04
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In particular, the use of chiral triazolecarbenes as ligands in allylic substitution reactions has not been reported so far

Method used

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  • Metal iridium complex, monocrystal, benzoindole compound, and synthesis method and applications thereof
  • Metal iridium complex, monocrystal, benzoindole compound, and synthesis method and applications thereof
  • Metal iridium complex, monocrystal, benzoindole compound, and synthesis method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] The synthesis of the metal iridium complex shown in embodiment 1 general formula I

[0086]

[0087] Under argon protection, in a dry 250 ml three-neck flask, add [Ir(cod)Cl] 2 (336 mg, 0.5 mmol), the compound represented by formula a and a base were added with an organic solvent and stirred for 24 hours. The crude product was separated by column chromatography (ethyl acetate / petroleum ether=1:5). See Table 1 for the specific reaction conditions of Compounds Ia-Ic and Compound If. Compound Id-Ie, the preparation method and condition of compound Ig-Ik are with reference to embodiment 1 and table 1, and wherein, the molar ratio in table 1 refers to [Ir(cod) × 1 ] 2 : molar ratio of compound a: base.

[0088] Table 1

[0089]

[0090] Compound Ia

[0091]

[0092] Yellow solid, yield: 54%. (purity>97%, NMR purity)

[0093] 1 H NMR (300MHz, CDCl 3 )δ8.32 (d, J = 7.2Hz, 2H), 7.49-7.46 (m, 3H), 4.94 (AB, J AB =15.0Hz, 1H), 4.80-4.71(m, 3H), 4.44-4.38(m, 2H),...

Embodiment 2

[0148] The synthesis of the metal iridium complex shown in embodiment 2 general formula II

[0149]

[0150] Under argon protection, in a dry 250 ml three-necked bottle, add [Ir(cod)X 1a ] 2 (336mg, 0.5mmol), the compound represented by formula b and a base, an organic solvent, stirred and reacted, and the crude product was separated by column chromatography (ethyl acetate / petroleum ether: 1:5). See Table 2 for the specific reaction conditions of compounds IIa-IIc and compound IIf. Compound IId-IIe, the preparation method and condition of compound IIg-IIu are with reference to embodiment 2 and table 2, wherein, the molar ratio in table 2 refers to [Ir(cod)× 1a ] 2 : molar ratio of compound b: base.

[0151] Table 2

[0152]

[0153] Compound IIa

[0154]

[0155] Yellow solid, yield: 55%. (purity>97%, NMR purity)

[0156] MS (ESI + ):858(C 39 h 42 ikB 4 o 2 S[M + ]).

[0157] Compound IIb

[0158]

[0159] Yellow solid, yield: 56%. (purity>97%, NMR p...

Embodiment 3

[0233] Embodiment 3 is as the synthesis of metal iridium complex shown in formula III

[0234]

[0235] Under argon protection, in a dry 250 ml three-necked bottle, add [Ir(cod)X 1b ] 2 (336mg, 0.5mmol), the compound represented by formula c and a base, an organic solvent, reacted with stirring. The crude product was separated by column chromatography (ethyl acetate / petroleum ether: 1:5). See Table 3 for the specific reaction conditions of compounds IIIa-IIIc and compound IIIf. The preparation method and condition of compound IIId-IIIe refer to embodiment 3 and table 3, wherein, the molar ratio in table 3 refers to [Ir(cod)× 1b ] 2 : molar ratio of compound c: base.

[0236] table 3

[0237]

[0238]

[0239] MS (ESI + ):1244(C 44 h 45 CIF 17 IrN 4 o 2 S[M + ]).

[0240] Compound IIIa

[0241]

[0242] Yellow solid, yield: 61%. (purity>97%, NMR purity)

[0243] MS (ESI + ):579(C 22 h 29 ikB 3 O[M + ]).

[0244] The preparation method of compound...

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Abstract

The invention discloses a metal iridium complex, a monocrystal, a benzoindole compound, and a synthesis method and applications thereof. According to the synthesis method, in an organic solvent, in the presence of an alkali, a chiral triazole carbene salt is subjected to complexation with [Ir(cod)X<1>]2, [Ir(cod)X<1a>]2, [Ir(cod)X<1b>]2, [Ir(cod)X<1c>]2, [Ir(cod)X<1d>]2, or [Ir(cod)X<1e>]2 respectively. The invention also discloses applications of the metal iridium complex as a catalyst in asymmetrical allylic substitution. According to the metal iridium complex, triazole carbine is taken as a ligand; the synthesis method and postprocessing are both simple; and excellent effect is achieved in metal iridium catalyzed asymmetrical allylic substitution.

Description

technical field [0001] The invention relates to a metal iridium complex, a single crystal, a benzindole compound, a synthesis method and an application. Background technique [0002] Metal iridium-catalyzed asymmetric allyl substitution reactions can construct carbon-carbon bonds and carbon-heterobonds with high enantioselectivity and regioselectivity, and have been widely used in synthesis. The catalyst currently used in this type of reaction is mainly [Ir(cod)Cl] 2 and chiral phosphine nitrogen ligands [(a) Miyabe, H.; Takemoto, Y.Synlett2005, 1641. (b) Takeuchi, R.; Kezuka, S.Synthesis2006, 3349. (c) Helmchen, G.; Dahnz, A.; Dübon, P.; Schelwies, M.; Weihofen, R. Chem. Commun. 2007, 675. (d) Helmchen, G.; In Iridium Complexes in Organic Synthesis; Oro, L.A.; Claver, C. Eds. ; Wiley-VCH: Weinheim, Germany, 2009; p 211. (e) Hartwig, J.F.; Stanley, L.M. Acc. Chem. Res. 2010, 43, 1461. (f) Hartwig, J.F.; Pouy, M.J. Chem.2011,34,169.(g)Liu,W.-B.; Xia,J.-B.;You,S.-L.Top.Orga...

Claims

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Application Information

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IPC IPC(8): C07F15/00B01J31/22C07D487/04
Inventor 游书力叶克印吴可嘉
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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