Synthesis and Properties of Bis(2-heteroaryl)borane Derivatives

Köhler, Thorsten; Faderl, Jürgen; Pritzkow, Hans; Siebert, Walter

doi:10.1002/1099-0682(200211)2002:11<2942::aid-ejic2942>3.0.co;2-p

Cited by 24 publications

(5 citation statements)

References 7 publications

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“…[49] Later the author engaged a similar approach for the synthesis of bis-heteroaryl boranes (Scheme 7b). [50] In 2007 the Klingensmith and Moniz group reported the synthesis of 4-methyl-2-thiopheneboronic anhydride (Scheme 7c). [51] Regioselective lithiation of 3-methyl thiophene followed by its quenching with triisopropyl borate gives 4-methyl-2-thiopheneboronic ester as a major product.…”

Section: Through Lithiation-borylationmentioning

confidence: 99%

“…Treatment of 1‐methylpyrrole with excess of n BuLi and TMEDA affords 2,5‐dilthio‐1‐methylpyrrole, which reacted with ClB(NMe 2 ) 2 to give 2,5‐bis[bis(dimethylamino)boryl]‐1‐methylpyrrole in 47 % yield (Scheme 7a) [49] . Later the author engaged a similar approach for the synthesis of bis‐heteroaryl boranes (Scheme 7b) [50] . In 2007 the Klingensmith and Moniz group reported the synthesis of 4‐methyl‐2‐thiopheneboronic anhydride (Scheme 7c) [51] .…”

Section: Through Dehydrogenative Pathwaymentioning

confidence: 99%

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Transition‐Metal‐Free Heterocyclic Carbon‐Boron Bond Formation

Hazra

Mahato

Das

et al. 2022

Chemistry A European J

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Heteroaryl boronic acids and esters are extremely important and valuable intermediates because of their wide application in the synthesis of marketed drugs and bioactive compounds. Over the last couple of decades, the construction of highly important heteroaryl carbon‐boron bonds has created huge attention. The transition‐metal‐free protocols are more green, less sensitive to air and moisture, and also economically advantageous over the transition‐metal‐based protocols. The transition‐metal‐free C−H borylation of heteroarenes and C−X (X=halogen) borylation of heteroaryl halides represents an excellent approach for their synthesis. Also, various cyclization and alkyne activation protocols have been recently established for their synthesis. The goal of this review article is to summarize the existing literature and the current state of the art for transition‐metal‐free synthesis of heteroaryl boronic acid and esters.

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Section: Through Lithiation-borylationmentioning

confidence: 99%

Section: Through Dehydrogenative Pathwaymentioning

confidence: 99%

Transition‐Metal‐Free Heterocyclic Carbon‐Boron Bond Formation

Hazra

Mahato

Das

et al. 2022

Chemistry A European J

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“…The [2 ϩ 2] cyclization of dibromo derivatives gives the first N-methylpyrrole containing tetraboraporphyrinogen. 172 Neutral N-borane-protected 1,1Ј-bisimidazoles can be synthesized by addition of BH 3 ؒTHF to the parent imidazoles. Deprotonation results in bis-"Arduengo" carbenes, which have been chelated to {Cp 2 Ti} fragments and show both Ti-carbene and Ti ؒ ؒ ؒ H 3 B interactions XVII.…”

Section: Boron-pnictogen Complexesmentioning

confidence: 99%

3 Boron

Weller

2003

Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem.

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“…An important recent finding in this regard was that the combination of furan rings with strongly electron-withdrawing groups substantially improves their resistance to oxidative degradation by lowering the compound’s highest occupied molecular orbital (HOMO) energy and therefore enhancing its overall stability. ,− The doping of conjugated π systems with trivalent boron atoms has emerged as an effective strategy to produce novel compounds with intriguing properties and functions. − …”

Section: Introductionmentioning

confidence: 99%

Boron-Doped α-Oligo- and Polyfurans: Highly Luminescent Hybrid Materials, Color-Tunable through the Doping Density

et al. 2021

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Doping of π-conjugated polymers or molecular compounds with trivalent boron atoms has recently emerged as a viable strategy to produce new materials with intriguing properties and functions. The combination of boron with furan moieties has been only scarcely explored so far, although the resulting furan-based materials have several notable features, including favorable optoelectronic properties and improved sustainability. Herein, we investigate the doping of α-polyfurans with a varying number of boron atoms. A series of poly(oligofuran boranes) and oligofuran-bridged bisboranes have been prepared via microwave-assisted Stille-type catalytic cross-coupling protocols. In the solid-state structures of the molecular compounds, the furan and the borane moieties exhibit a strictly coplanar arrangement; the derivative with a pentafuran bridge forms a dimeric structure in the solid state. All new compounds show considerable absorption and emission features in the visible range that arise from π–π* transitions in the oligofurylborane backbone. They are highly luminescent with quantum yields between 89 and 97% for the bisboranes and up to 87% for the difuran-bridged polymer PB2F. Their emission colors can be effectively tuned in the visible range from blue to orange via the length of the oligofuran linker. Spectroelectrochemical investigations on the difuran-bridged bisborane BB2F and polymer PB2F revealed fully reversible stepwise reductions to the respective radical anion (polaron), with absorption features in the near-infrared (NIR) region, and subsequently to a dianion (dipolaron). Overall, the doping of α-oligofurans with boron leads to a decrease of the frontier orbital energies, a reduction of the electronic band gap, and the formation of very robust and oxidatively stable materials.

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Synthesis and Properties of Bis(2-heteroaryl)borane Derivatives

Cited by 24 publications

References 7 publications

Transition‐Metal‐Free Heterocyclic Carbon‐Boron Bond Formation

Transition‐Metal‐Free Heterocyclic Carbon‐Boron Bond Formation

3 Boron

Boron-Doped α-Oligo- and Polyfurans: Highly Luminescent Hybrid Materials, Color-Tunable through the Doping Density

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