Aryl(hydro)boranes: versatile building blocks for boron-doped π-electron materials

Lorbach, Andreas; Hübner, Alexander; Wagner, Mat­thias

doi:10.1039/c2dt30118k

Cited by 208 publications

(100 citation statements)

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“…[22] The reaction starts immediately and requires several days for completion. [4,13] The X-ray crystal structure analysis of (2) 2 together with DFT calculations on (2) 2 and selected simplified model systems allowed us to gain a comprehensive picture of the bonding situation in this molecule. [22] Correspondingly, (2) 2 A persists in non-dried CDCl 3 for weeks, whereas (A) 2 and (2) 2 are prone to hydrolysis (NMR spectroscopy control).…”

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Confirmation of an Early Postulate: BCB Two‐Electron–Three‐Center Bonding in Organo(hydro)boranes

et al. 2012

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Confirmation of an Early Postulate: BCB Two‐Electron–Three‐Center Bonding in Organo(hydro)boranes

et al. 2012

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“…In the past few decades, dihaloboryl-substituted arenes have gained significant importance as starting materials for aryl(hydro)boranes (Lorbach et al, 2012) and BN addition compounds (Heilmann-Brohl et al, 2011), for example. Both classes of substance feature intriguing optoelectronic behaviour.…”

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confidence: 99%

Structural characteristics of dibromoborylated benzene derivatives

et al. 2012

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The crystal structures of five dibromobenzene derivatives, namely dibromoborylbenzene, C(6)H(5)BBr(2), (I), 1-dibromoboryl-4-(trimethylsilyl)benzene, C(9)H(13)BBr(2)Si, (II), 4-bromo-1-(dibromoboryl)benzene, C(6)H(4)BBr(3), (III), dibromo(dimethylamino)(phenyl)borane, C(8)H(12)BBr(2)N, (IV), and dibromo(dimethylsulfanyl)[4-(trimethylsilyl)phenyl]borane, C(11)H(19)BBr(2)SSi, (V), have been determined. Compounds (I)-(IV) crystallize with one molecule in the asymmetric unit, but the molecule of (V) is located on a crystallographic mirror plane, implying twofold disorder of the central aromatic ring, the S atom and one of the methyl groups bonded to the S atom. In (I), (II) and (III), the B atom is three-coordinated, and in (IV) and (V) it is four-coordinated. The geometric parameters of the -BBr(2) group in these five structures agree well with those of comparable structures retrieved from the Cambridge Structural Database. The C-B and B-Br bond lengths in the molecules with a three-coordinated B atom are significantly shorter than those in the molecules with a four-coordinated B atom. In the compounds with a three-coordinated B atom, the -BBr(2) group tends to be coplanar with the aromatic ring to which it is attached.

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“…Boronic acids and esters are key materials in the areas of organic synthesis 1-3 , catalysis 4-6 , materials science 7,8 , drug discovery 9-11 , molecular self-assembly 12,13 , carbohydrate analysis 14-16 , and molecular sensing 17-20 . Photoinduced dissociation of Ar–X bonds has enabled a number of synthetically useful carbon–carbon and carbon–heteroatom bond-forming transformations, e.g.…”

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Metal- and additive-free photoinduced borylation of haloarenes

et al. 2017

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Boronic acids and esters have crucial roles in the areas of synthetic organic chemistry, molecular sensors, materials science, drug discovery, and catalysis. Many of the current applications of boronic acids and esters require materials with very low levels of transition metal contamination. Most of the current methods for the synthesis of boronic acids require, however, transition metal catalysts and ligands that have to be removed via additional purification procedures. This protocol describes a simple, metal- and additive-free method of conversion of haloarenes directly to boronic acids and esters. This photoinduced borylation protocol does not require expensive and toxic metal catalysts and ligands and produces innocuous and easy-to-remove by-products. Furthermore, the reaction can be carried out on multigram scales in common grade solvents without the need for reaction mixtures to be deoxygenated. The setup and purification steps are typically accomplished within 1–3 h. The reactions can be run overnight, and the protocol can be completed within 13–16 h. Two representative procedures that are described in this protocol provide details for preparation of a boronic acid (3-cyanopheylboronic acid) and a boronic ester (1,-benzenediboronic acid bis(pinacol)ester). We also discuss additional details of the method that will be helpful in the application of the protocol to other haloarene substrates.

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Aryl(hydro)boranes: versatile building blocks for boron-doped π-electron materials

Cited by 208 publications

References 262 publications

Confirmation of an Early Postulate: BCB Two‐Electron–Three‐Center Bonding in Organo(hydro)boranes

Confirmation of an Early Postulate: BCB Two‐Electron–Three‐Center Bonding in Organo(hydro)boranes

Structural characteristics of dibromoborylated benzene derivatives

Metal- and additive-free photoinduced borylation of haloarenes

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