π‐Extended Pleiadienes by [5+2] Annulation of 1‐Boraphenalenes and <i>ortho</i>‐Dihaloarenes

Schnitzlein, Matthias; Zhu, Chongwei; Shoyama, Kazutaka; Würthner, Frank

doi:10.1002/chem.202202053

Cited by 9 publications

(3 citation statements)

References 53 publications

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“…Three-coordinate NHC-borenium cations are strongly electrophilic boron compounds that can be generated from the air- and moisture-stable NHC-boranes and a strong acid. Würthner et al recently developed a synthesis of cyclic borinic acids relying on this chemistry study ( Scheme 29 ); the NHC-borenium species is first generated from 1,3-diisopropylimidazol-2-ylidene borane 91 and HNTf 2 [ 67 , 68 , 69 , 70 ]. The subsequent addition of 92 , led to the cyclic NHC-borane intermediate 93 .…”

Section: Formation Of Two Carbon–boron Bondsmentioning

confidence: 99%

Recent Advances in the Synthesis of Borinic Acid Derivatives

2023

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Borinic acids [R2B(OH)] and their chelate derivatives are a subclass of organoborane compounds used in cross-coupling reactions, catalysis, medicinal chemistry, polymer or optoelectronics materials. In this paper, we review the recent advances in the synthesis of diarylborinic acids and their four-coordinated analogs. The main strategies to build up borinic acids rely either on the addition of organometallic reagents to boranes (B(OR)3, BX3, aminoborane, arylboronic esters) or the reaction of triarylboranes with a ligand (diol, amino alcohol, etc.). After general practical considerations of borinic acids, an overview of the main synthetic methods, their scope and limitations is provided. We also discuss some mechanistic aspects.

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Section: Formation Of Two Carbon–boron Bondsmentioning

confidence: 99%

Recent Advances in the Synthesis of Borinic Acid Derivatives

2023

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“…Following this synthetic strategy, they further developed two BMCs 25 and 26 using the corresponding alkenes. 18d e Interestingly, Pd-catalyzed [5 + 2] annulation with suitable aryl dihalides toward 25 or 26 generates carbon-based MCs that feature seven-membered rings. This method is very useful to expand the scope of available nonplanar MCs with both positive and negative curvatures.…”

Section: Polycyclic Boron-doped Molecular Carbonsmentioning

confidence: 99%

Progress of Polycyclic Boron-Doped Molecular Carbons

Yuan,

Wang,

Dou

2023

Organic Materials

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Molecular carbons, namely molecular cutout of carbon materials, are of importance for understanding accurate structures of carbon allotropes and developing functional π-electron materials. Doping the boron atoms into π-conjugated skeletons of molecular carbons enables the construction of boron-doped molecular carbons (BMCs), further leading to new chemistry and attractive material systems, which are distinct from carbon-based and other heteroatom-doped molecular carbons. Herein, the bottom-up organic synthesis methodologies have been employed to synthesize BMCs that feature the boron atoms at the edge or in the centre of π-skeletons. They have not only amazing topological structures and good stability but also intriguing photophysical and electronic properties. Moreover, they have sufficient Lewis acidity and can coordinate with Lewis bases to form Lewis acid-base complexes, which exhibit stimuli-responsive functions. Notably, some of these BMCs can be utilized in the fields of organic reactions, optical and electronic devices, as well as supramolecular chemistry and photothermal materials. In this short review, we aim to highlight the design and synthetic strategies of polycyclic BMCs, and their unique physical properties and practical applications.

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“…In contrast to the well-explored progress in the preparation of five or six-membered planar fused polycycles and their fascinating photophysical and electronic properties, the studies on the synthesis of seven-membered π-conjugated systems are still underdeveloped, because of the transannular strain of seven-membered rings. Progress in the investigation of polyaromatic hydrocarbons containing planar heptagon(s), such as pleiadiene 4 or nanographene, 5 exhibiting excellent optical and redox properties was achieved. The last decade also witnessed increasing attention on π-conjugated cycloheptatrienes containing a heteroatom, namely heteropins (Scheme 1a).…”

Section: Introductionmentioning

confidence: 99%