Tandem Suzuki Coupling−Norbornadiene Insertion Reactions. A Convenient Route to 5,6-Diarylnorbornene Compounds

Shaulis, Katie M.; Hoskin, Bradley L.; Townsend, John C.; Goodson, Felix E.; Incarvito, Christopher D.; Rheingold, Arnold L.

doi:10.1021/jo016212b

Cited by 43 publications

(26 citation statements)

References 30 publications

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“…Later in 1998, Kang and coworkers also demonstrated that Pd‐catalysts could catalyze the selective difunctionalization of one olefin in norbornadiene with ArN 2 BF 4 or Ph 2 IBF 4 and a variety of nucleophiles such as alkynes, PhSnBu 3 , NaBPh 4 and PhB(OH) 2 (Scheme ) . A similar reaction of selective difunctionalization of one olefin in norbornadiene was also reported by Goodson and coworkers by using aryl halides and ArB(OH) 2 as carbon sources in the presence of Pd(OAc) 2 as a catalyst (Scheme ) …”

Section: Intermolecular Dicarbofunctionalization Of Olefinsmentioning

confidence: 99%

Transition Metal‐Catalyzed Dicarbofunctionalization of Unactivated Olefins

Dhungana

Basnet

et al. 2018

The Chemical Record

377

116

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Transition metal (TM)-catalyzed difunctionalization of unactivated olefins with two carbon-based entities is a powerful method to construct complex molecular architectures rapidly from simple and readily available feedstock chemicals. While dicarbofunctionalization of unactivated olefins has a long history typically with the use of either carbon monoxide to intercept C(sp )-[M] (alkyl-TM) species or substrates lacking in β-hydrogen (β-Hs), development of this class of reaction still remains seriously limited due to complications of β-H elimination arising from the in situ-generated C(sp )-[M] intermediates. Over the years, different approaches have been harnessed to suppress β-H elimination, which have led to the development of various types of olefin dicarbofunctionalization reactions even in substrates that generate C(sp )-[M] intermediates bearing β-Hs with a wide range of electrophiles and nucleophiles. In this review, these developments will be discussed both through the lens of historical perspectives as well as the strategies scrutinized over the years to address the issue of β-H elimination. However, this review article by no means is designed to be exhaustive in the field, and is merely presented to provide the readers an overview of the key reaction developments.

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Section: Intermolecular Dicarbofunctionalization Of Olefinsmentioning

confidence: 99%

Transition Metal‐Catalyzed Dicarbofunctionalization of Unactivated Olefins

Dhungana

Basnet

et al. 2018

The Chemical Record

377

116

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“…[59] Therefore,norbornenes with definite configuration produced by stereoselective reaction are necessary for controlling alignment of the substituents (that is,d onor and acceptor). Herein, at andem Suzuki coupling-norbornadiene insertion reaction of aryl iodide and arylboronic ester in presence of norbornadiene [60] is used for preparation of disubstituted monomers because they can selectively afford cis, exo-isomers in which donor and acceptor are aligned in the same side of norbornene skeleton. By using Pd(OAc) 2 /PPh 3 as catalyst, three disubstituted norbornene monomers are obtained.…”

Section: Molecular Design and Synthesismentioning

confidence: 99%

Through‐Space Charge‐Transfer Polynorbornenes with Fixed and Controllable Spatial Alignment of Donor and Acceptor for High‐Efficiency Blue Thermally Activated Delayed Fluorescence

et al. 2020

Angewandte Chemie

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Through-space charge transfer polynorbornenes with fixeda nd controllable spatial alignment of donor and acceptor in edge-to-face/face-to-face stacking patterns are developed for achieving high-efficiency blue thermally activated delayed fluorescence (TADF). The alignment is realized by using the cis,e xo-configuration of norbornene to confine donor and acceptor in close proximity, and utilizing orthogonal and dendritic structures of donors to provide either perpendicular or parallel stackingm otif relative to acceptors. Compared to edge-to-face counterparts,polynorbornenes with face-to-face aligned donor and acceptor exhibit muchl arger oscillator strength and higher photoluminescence quantum yield. The resulting polymers exhibit deep blue (422 nm) to sky blue (482 nm) emission and TADF effect with reverse intersystem crossing rates of 0.4-5.9 10 6 s À1 ,giving the maximum external quantum efficiency of 18.8 %f or non-doped blue organic light-emitting diodes by solution process.

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“…In line with this, a great deal of interest has been devoted to norbornene 1 and its analogues [6][7]. Syncarbopalladation of these alkenes with aryl or vinyl halides may be terminated by stereoselective trapping with nucleophiles such as alkenyl stannanes 2 (Stille coupling) [7], terminal acetylenes 3 (Cassar/Sonogashira coupling) [8,9], tetraaryl borates 4 [10] and boronic acids 5 (Suzuki coupling) [11,12], or cyanide ion [13] (Scheme 8.1). Scheme 8.2 illustrates the potential applications of such vicinal difunctionalization reactions to the construction of leucotriene model compounds 6 [14].…”

Section: Carbopalladation Of Norbornene and Its Analoguesmentioning

confidence: 99%