[Cp*IrCl2]2 catalyzed hydroborations of alkenes using a bulky dioxaborocine

Hunter, Nicole Marie; Vogels, Christopher M.; Decken, Andreas; Bell, Andrew; Westcott, Stephen A.

doi:10.1016/j.ica.2010.09.051

Cited by 11 publications

(4 citation statements)

References 49 publications

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“…5, green triangles) all of them have positive v y values and the corresponding points in the projection on the xy plane are located in the upper region of six-membered ring representatives. This effect is particularly pronounced in the case of EKOGOB (Hunter et al, 2011) with the resultant vector of 0.12 v.u. Hence, in the case of cyclic esters the ring-size effect appears to be the main factor influencing the boron coordination sphere geometry, which consists of widening of the OBO angle together with an increasing number of atoms in the ring.…”

Section: Figurementioning

confidence: 95%

Geometry of trigonal boron coordination sphere in boronic acids derivatives – a bond-valence vector model approach

Czerwińska

Madura

Zachara

2016

Acta Crystallogr Sect B

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The systematic analysis of the geometry of three-coordinate boron in boronic acid derivatives with a common [CBO2] skeleton is presented. The study is based on the bond-valence vector (BVV) model [Zachara (2007). Inorg. Chem. 46, 9760-9767], a simple tool for the identification and quantitative estimation of both steric and electronic factors causing deformations of the coordination sphere. The empirical bond-valence (BV) parameters in the exponential equation [Brown & Altermatt (1985). Acta Cryst. B41, 244-247] rij and b, for B-O and B-C bonds were determined using data deposited in the Cambridge Structural Database. The values obtained amount to rBO = 1.364 Å, bBO = 0.37 Å, rBC = 1.569 Å, bBC = 0.28 Å, and they were further used in the calculation of BVV lengths. The values of the resultant BVV were less than 0.10 v.u. for 95% of the set comprising 897 [CBO2] fragments. Analysis of the distribution of BVV components allowed for the description of subtle in- and out-of plane deviations from the `ideal' (sp(2)) geometry of boron coordination sphere. The distortions specific for distinct groups of compounds such as boronic acids, cyclic and acyclic esters, benzoxaboroles and hemiesters were revealed. In cyclic esters the direction of strains was found to be controlled by the ring size effect. It was shown that the syn or anti location of substituents on O atoms is decisive for the deformations direction for both acids and acyclic esters. The greatest strains were observed in the case of benzoxaboroles which showed the highest deviation from the zero value of the resultant BVV. The out-of-plane distortions, described by the vz component of the resultant BVV, were ascertained to be useful in the identification of weak secondary interactions on the fourth coordination site of the boron centre.

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Section: Figurementioning

confidence: 95%

Geometry of trigonal boron coordination sphere in boronic acids derivatives – a bond-valence vector model approach

Czerwińska

Madura

Zachara

2016

Acta Crystallogr Sect B

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“…In particular, norbornene and derivatives have been investigated extensively as substrates in catalytic hydroborations. 33,35,76,77,86,[97][98][99][100]125,146,[154][155][156][157]163,[176][177][178][179][180][181][182][183][184][185][186][187][188][189] Transition metal-catalysed hydroborations are selective for giving the exo-hydroboration products. Several chiral ligands have also been used for the asymmetric hydroboration of these substrates, however many chiral rhodium complexes offered only modest levels of enantioselectivity.…”

Section: 2-disubstituted Aliphatic Alkenesmentioning

confidence: 99%

The transition metal-catalysed hydroboration reaction

et al. 2022

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“…Commonly used boranes in both unanalyzed and catalyzed hydroboration reactions are pinacolborane (HBO2C2Me4) and catecholborane (HBO2C6H4), both of which are derived from 1,2-diols. Likewise, our recent efforts in this area have involved the synthesis of sterically-encumbered dioxaborolanes derived from commercially-accessible 1,2-diols that are easily handled and stored for the selective addition to alkenes and alkynes [4,5]. Much less studied, however, are hydroboranes based on amines and aminoalcohols.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Reactivity of Novel Boranes Derived from Bulky Salicylaldimines: The Molecular Structure of a Maltolato Compound

et al. 2015

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Reductive amination of salicylaldehyde or 3,5-di-tert-butylsalicylaldehyde and 1-adamantylamine using NaBH4 gave the corresponding aminoalcohols in high yields. Subsequent addition of one equivalent of H3B·SMe2 to the aminoalcohols, with loss of two equivalents of dihydrogen, resulted in the formation of adamantanyl oxazaborinanes (1a,b). The molecular structure of 1b was studied by a single crystal X-ray diffraction study. Crystals were obtained from a saturated Et2O solution and belong to the triclinic space group Pī with unit cell parameters a = 9.1267(4) Å; b = 11.676(2) Å; c = 12.240(3) Å; α = 66.840(3)°; β = 78.529(3)°; and γ = 67.354(3)°. The molecular structure of the addition product (2a) arising from maltol and 1a was also confirmed by single crystal X-ray diffraction. Crystals were obtained from a saturated 1:2 mixture of toluene/Et2O and belong to the orthorhombic space group Pna2(1) with unit cell parameters a = 18.519(6) Å; b = 17.315(5) Å; and c = 12.680(4) Å. The asymmetric unit contains two molecules that differ slightly in some of the dihedral angles.

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[Cp*IrCl2]2 catalyzed hydroborations of alkenes using a bulky dioxaborocine

Cited by 11 publications

References 49 publications

Geometry of trigonal boron coordination sphere in boronic acids derivatives – a bond-valence vector model approach

Geometry of trigonal boron coordination sphere in boronic acids derivatives – a bond-valence vector model approach

The transition metal-catalysed hydroboration reaction

Synthesis and Reactivity of Novel Boranes Derived from Bulky Salicylaldimines: The Molecular Structure of a Maltolato Compound

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