Rigid tetraarylene-bridged cavitands from reduced-symmetry resorcin[4]arene derivatives

Smith, Jordan N.; Lucas, Nigel T.

doi:10.1039/c8cc01903g

Cited by 27 publications

(26 citation statements)

References 34 publications

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“…Smith and Lucas have reported the synthesis of interesting tetraarylene‐bridged cavitands based on resorcin[4]arene using FeCl 3 or DDQ as the oxidants …”

Section: Intramolecular Oxidative Aromatic Couplingmentioning

confidence: 99%

“…Smith and Lucas have reported the synthesis of interesting tetraarylene-bridged cavitands based on resorcin [4]arene using FeCl 3 or DDQ as the oxidants. [222] Helicenes have fired researchers imagination ever since the first synthesis and resolution of [6]helicene in 1956. [223] Thesynthesis of helicenes has long been dominated by iodinecatalyzed photocyclizations of stilbene derivatives.…”

Section: Curved Twisted and Strained Structuresmentioning

confidence: 99%

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Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

et al. 2019

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Oxidative aromatic coupling occupies a fundamental place in the modern chemistry of aromatic compounds. It is a method of choice for the assembly of large and bewildering architectures. Considerable effort was also devoted to applications of the Scholl reaction for the synthesis of chiral biphenols and natural products. The ability to form biaryl linkages without any prefunctionalization provides an efficient pathway to many complex structures. Although the chemistry of this process is only now becoming fully understood, this reaction continues to both fascinate and challenge researchers. This is especially true for heterocoupling, that is, oxidative aromatic coupling with the chemoselective formation of a C−C bond between two different arenes. Analysis of the progress achieved in this field since 2013 reveals that many groups have contributed by pushing the boundary of structural possibilities, expanding into surface‐assisted (cyclo)dehydrogenation, and developing new reagents.

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“…Smith and Lucas have reported the synthesis of interesting tetraarylene‐bridged cavitands based on resorcin[4]arene using FeCl 3 or DDQ as the oxidants …”

Section: Intramolecular Oxidative Aromatic Couplingmentioning

confidence: 99%

Section: Curved Twisted and Strained Structuresmentioning

confidence: 99%

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

et al. 2019

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“…One promising approach is to take advantage of conveniently synthesized cyclophanes or macrocycles, which can serve as precursors for synthesis of new conjugated nanobelts. This approach has already received preliminary success in the very recent syntheses of hydrocarbon nanobelts by Lucas, [ 51 ] Wang, [ 47,52 ] and Itami. [ 53 ]…”

Section: Discussionmentioning

confidence: 99%

“…Stępień and coworkers in 2014 synthesized 87 (Scheme 14a), a heptagon‐embedded nanobelt, from macrocycle 86 using a “fold‐in” strategy. [ 50 ] The groups of Lucas and Wang reported synthesis of heptagon‐embedded nanobelts from resorcarenes in 2018 [ 51 ] and 2020, [ 52 ] respectively. Scheme 14b shows the ladderization step in Lucas' synthesis of nanobelt 89 through the Scholl reaction of a resorcin[4]arene derivative ( 88 ).…”

Section: Attempts and Success In The Synthesis Of Conjugated Nanobeltsmentioning

confidence: 99%

Recent advances and attempts in synthesis of conjugated nanobelts

Chen

Miao

2020

J of Physical Organic Chem

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Conjugated nanobelts are attractive molecules of esthetic appeal, synthetic challenges, unique properties, interesting applications, and potential impacts. The recent years have witnessed significant progress in the synthesis of carbon nanobelts and approaches to a new type of conjugated nanobelts. This review emphasizes two general synthetic strategies to approach conjugated nanobelts, and briefly covers structurally related nanobelts that are not fully conjugated, and finally provides an outlook for new directions in the field.

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“…[17] For the fenestrindane core, quadruple cycloheptatriene generation successfully led to the saddle-shaped derivatives 6(34diOMe)Q, 6(234triOMe)Q and 6(3OEt4OMe)Q. [18] Re-cently,arigid cavitand 7,b earing four cycloheptatriene units, was synthesized by Lucas utilizing as imilar strategy, [19] which furtherd emonstrated the usefulness of this type of cyclization.…”

Section: Introductionmentioning

confidence: 99%

Scholl‐Type Cycloheptatriene Ring Closure of 1,4,9,12‐Tetraarylfenestrindanes: Reactivity and Selectivity in the Construction of Fenestrane‐Based Polyaromatic Saddles

Wong

Lau

et al. 2020

Chemistry A European J

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The Scholl‐type cyclodehydrogenation, generating up to four cycloheptatriene rings around a fenestrindane core, leads to novel, saddle‐shaped polyaromatic hydrocarbon derivatives. In this article, we present the results of in‐depth experimental and computational work on the oxidative cyclization of various 1,4,9,12‐tetraarylfenestrindanes. In particular, the kinetic control of the four‐step cyclization of the electronically activated tetrakis(3,4‐dimethoxyphenyl) derivative is elucidated. The reasons for the exclusive emergence of one single among the three possible doubly cyclized intermediates and for the nonappearance of the singly and triply cyclized intermediates are clarified. In addition, the origin of the concomitant bridgehead hydroxylation is studied. The reactivity of a set of fifteen symmetrically and unsymmetrically substituted 1,4,9,12‐tetraarylfenestrindanes towards Scholl‐type cyclodehydrogenation is presented, pinpointing the structural factors that underlie this reaction and demonstrating the potential and limitations of this synthetic approach. A particularly surprising finding of this study is that the electronically nonactivated 1,4,9,12‐tetraphenylfenestrindane can also undergo the fourfold Scholl‐type cyclization process and can be transformed into the parent saddle hydrocarbon.

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Rigid tetraarylene-bridged cavitands from reduced-symmetry resorcin[4]arene derivatives

Abstract: Two tetraaryl-extended macrocycles were prepared from resorcin[4]arenes. The C2v-symmetric isomer afforded a new rigid cyclooctaphenylene cavitand following oxidative cyclodehydrogenation.

Cited by 27 publications

References 34 publications

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

Recent advances and attempts in synthesis of conjugated nanobelts

Scholl‐Type Cycloheptatriene Ring Closure of 1,4,9,12‐Tetraarylfenestrindanes: Reactivity and Selectivity in the Construction of Fenestrane‐Based Polyaromatic Saddles

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