1:1 and 2:1 Lithium Zincates with Intramolecular Coordination. Structures of Li(thf)Zn(C6H4CH2NMe2-2)3 and Li2Zn(C6H4CH2NMe2-2)4

Koten, Gerard van; Rijnberg, Evelien; Jastrzebski, Johann T. B. H.; Boersma, J.; Kooijman, Huub; Veldman, Nora; Spek, Anthony L.

doi:10.1021/om9610307

Cited by 40 publications

(30 citation statements)

References 27 publications

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“…1 9 , or zinc and a metal like lithium, e.g. 2 10 , copper 3a or gold, e.g. 3b 11 , or aluminium have been observed, or have been proposed in a few cases ( Figure 1).…”

Section: Znmentioning

confidence: 99%

“…The structure of 11 in the solid state ( Figure 7) was established by an X-ray crystal structure determination 10 . The four aryl groups are η 1 -bonded to the central zinc atom with bonding distances ranging from 2.124(4) to 2.152(3)Å.…”

Section: {[(Mementioning

confidence: 99%

“…Zn (2) C(4) Zn]Li(THF) (23) was obtained, whose structure in the solid state was established by an Xray crystal structure determination 10 . Compound 23 does not comprise (solvent) separated ions, but both in the solid state and in solution this compound exists as a neutral species.…”

Section: {[(Mementioning

confidence: 99%

“…Et 3 + cation has a slightly distorted tetrahedral geometry as a result of the coordination of three additional diethyl ether molecules. The C−Zn−O bond angles range from 115.37 (10) • to 123.60 (9) • . The Zn−C(1) bond distance of 1.964 (3) 4 − , has been reported.…”

Section: B Monoorganozinc Cationsmentioning

confidence: 99%

“…Ethylzinc ethyl sulfide is a decamer (EtZnSEt) 10 . In this cluster all sulfide groups are µ 3 -bonded to three zinc atoms ( Figure 108).…”

Section: T-bu T-bu T-bu T-bu T-bu T-bumentioning

confidence: 99%

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Structural Organozinc Chemistry

Jastrzebski¹,

Boersma²,

Koten³

2006

The Chemistry of Organozinc Compounds

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“…1 9 , or zinc and a metal like lithium, e.g. 2 10 , copper 3a or gold, e.g. 3b 11 , or aluminium have been observed, or have been proposed in a few cases ( Figure 1).…”

Section: Znmentioning

confidence: 99%

Section: {[(Mementioning

confidence: 99%

Section: {[(Mementioning

confidence: 99%

Section: B Monoorganozinc Cationsmentioning

confidence: 99%

“…Ethylzinc ethyl sulfide is a decamer (EtZnSEt) 10 . In this cluster all sulfide groups are µ 3 -bonded to three zinc atoms ( Figure 108).…”

Section: T-bu T-bu T-bu T-bu T-bu T-bumentioning

confidence: 99%

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Structural Organozinc Chemistry

Jastrzebski¹,

Boersma²,

Koten³

2006

The Chemistry of Organozinc Compounds

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Zinc: Organometallic ChemistryBased in part on the article Zinc: Organometallic Chemistry by Gerard Parkin which appeared in theEncyclopedia of Inorganic Chemistry, First Edition.

Gr��vy¹

2005

Encyclopedia of Inorganic Chemistry

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Since the discovery of the first organozinc compounds by Sir Edward Frankland in 1849, the organometallic chemistry of zinc made remarkable advances and organozinc species have become essential tools for organic chemists. During the past decade, numerous new and modified procedures for the preparation of the title compounds have been published, rendering their synthesis easier, faster, and less expensive and giving higher yields. The coordination chemistry of organozinc derivatives has been subject of further interest and various intra‐ and intermolecular complexes with different donor ligands have been structurally characterized by X‐ray crystallography and spectroscopic methods. The accumulation of molecular structures, physicochemical studies, and computational calculations has led to a better understanding of the organozinc chemistry, and consequently to the design of new derivatives for specific applications. Even if the development of areas like the chemistry of organozinc anions and cations is still in its early stage, these compounds, which exhibit properties different than those of the parent organometallic species, appear to have promising applications in synthesis and catalytic reactions. During the past ten years, the chemistry of organo‐ gem ‐dizincio derivatives has also been the subject of much interest and progress. These reagents can form two carbon–carbon bonds in a one‐pot reaction and with high stereoselectivity. They became key reagents for organic chemists who want to combine multiple transformations in one operation. The importance of organometallic compounds of zinc can be seen in the growing number of their applications in synthesis. They are used in many reactions such as substitutions, additions to carbonyl compounds and unsaturated systems, cyclopropanations, and polymerizations. Furthermore, as a result of their low reactivity, they tolerate a wide variety of functionalities and perform most of the transformations with high regio‐ and enantioselectivity. After spending more than half a century in the shade of Grignard and organolithium reagents, organozinc reagents are becoming more and more important in modern chemistry.

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Oxygen Capture by Lithiated Organozinc Reagents Containing Aromatic 2-Pyridylamide Ligands

et al. 2001

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The sequential reaction of ZnMe2 with a 2-pyridylamine (HN(2-C5H4N)R, R = Ph: 1; 3,5-Xy (=3,5-xylyl): 2; 2,6-Xy: 3; Bz (=benzyl): 4; Me: 5), tBuLi and thereafter with oxygen affords various lithium zincate species, the solid-state structures of which reveal a diversity of oxo-capture modes. Amine 1 reacts to give both dimeric THF [Li(Me)OZn[N(2-C5H4N)Ph]2] (6), wherein oxygen has inserted into the Zn-C bond of a [MeZn[N(2-C5H4N)-Ph]2] ion, and the trigonal Li2Zn complex, bis(OtBu)-capped (THF x Li)2-[[(mu3-O)tBu]2Zn[N(2-C5H4N)Ph]2] (7). The structural analogue of 6 (8) results from the employment of 2, while the use of more sterically congested 3 yields a pseudo-cubane dimer [(THF x [Li(tBu)OZn(OtBu)Me]]2] (9) notable for the retention of labile Zn-C(Me). Amines 4 and 5 afford the oxo-encapsulation products [mu4-O)Zn4[(2-C5H4N)-NBz]6] (10b), and [tBu(mu3-O)-Li3(mu6-O)Zn3[(2-C5H4N)NMe]6] (11), respectively, with concomitant oxo-insertion into a Li-C interaction resulting in capping of the fac-isomeric (mu6-O)M3M'3 distorted octahedral core of the latter complex by a tert-butoxide group.

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1:1 and 2:1 Lithium Zincates with Intramolecular Coordination. Structures of Li(thf)Zn(C₆H₄CH₂NMe₂-2)₃ and Li₂Zn(C₆H₄CH₂NMe₂-2)₄

Cited by 40 publications

References 27 publications

Structural Organozinc Chemistry

Structural Organozinc Chemistry

Zinc: Organometallic ChemistryBased in part on the article Zinc: Organometallic Chemistry by Gerard Parkin which appeared in theEncyclopedia of Inorganic Chemistry, First Edition.

Oxygen Capture by Lithiated Organozinc Reagents Containing Aromatic 2-Pyridylamide Ligands

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