A Facile Synthesis of Blue Luminescent [7]Helicenocarbazoles Based on Gold‐Catalyzed Rearrangement‐Iodonium Migration and Suzuki–Miyaura Benzannulation Reactions

Alcaide, Benito; Almendros, Pedro; Aragoncillo, Cristina; Busto, Eduardo; López‐Calixto, Carmen G.; Liras, Marta; O’Shea, Víctor A. de la Peña; García-Sánchez, Alba; Stone, Hannah V.

doi:10.1002/chem.201801179

Cited by 11 publications

(4 citation statements)

References 32 publications

(27 reference statements)

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“…In 2018, Alcaide and co-workers reported the gold(I)catalyzed unique double cyclization involving cation migrations of C 2 -symmetric bis(indole)-1,3-diynes 78, leading to nonsymmetric diiodoheterobiaryls 79, as shown in Scheme 51. 279 These diiodoheterobiaryls 79 were subjected to the Suzuki− Miyaura cross-coupling annulation with diborylalkene derivatives 80 to give the corresponding [7]helicenocarbazoles 81 in moderate yield. 1,2-Diborylbenzene derivative 82 could also be used instead of 80 to give the corresponding triphenylene-based [7]helicenocarbazole 83.…”

Section: Helical Compoundsmentioning

confidence: 99%

Homogeneous and Heterogeneous Gold Catalysis for Materials Science

et al. 2020

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Often stoichiometric amounts of gold find use in materials science; occasionally gold is even used as a support. This review discusses the contributions of gold catalysis, both homogeneous and heterogeneous, to the field of materials science. One topic is the synthesis of polymers, including nanowires and polyesters, the postcyclization of polymers, polymerization by cyclopropanation, and gold-catalyzed radical polymerization reactions. Other topics are dyes, phosphonium salts, and a wide range of extended conjugated π-systems, the latter ranging from acenes, pentalene derivatives, and different heterocyclic π-systems to fascinating applications in the synthesis of helical anellated aromatic molecules. The existing contributions clearly demonstrate the potential of gold catalysis for significant future impulses for the field of materials science.

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Section: Helical Compoundsmentioning

confidence: 99%

Homogeneous and Heterogeneous Gold Catalysis for Materials Science

et al. 2020

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“…Subsequent Suzuki-Miyaura coupling with suitable boronic acids, the bis(iodocarbazoles) delivered final [7]helicenocarbazoles (Scheme 27). [42]…”

Section: Au-catalyzed 12-difunctionalizationsmentioning

confidence: 99%

Transition‐Metal‐Catalyzed Carbohalogenative 1,2‐Difunctionalization of C−C Multiple Bonds

2020

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Transition-metal-catalyzed 1,2-carbohalofunctionalization reactions of CÀ C multiple bonds have emerged rapidly over the past decade as a powerful tool for generating a new carbon-carbon and carbon-halogen bond via transposition of an existing carbon-halogen σ bond. Exploring this highly efficient mode of carbon-carbon multiple bond difunctionalization, various research groups have established novel strategies for the synthesis of organohalides by utilizing wide variety of transition metal catalysts under mild reaction conditions, avoiding stoichiometric waste of by-products, and with improved levels of chemo-, regio-, and stereoselectivities. Most of the 1,2-carbohalo-functionalization reactions involve either the carbon-halogen reductive elimination mechanism or the atom transfer radical addition (ATRA) mechanism. This review summarizes the recent progress in the area of transitionmetal-catalyzed intra-and intermolecular 1,2-carbo-halo-functionalization reactions of carbon-carbon multiple bonds and explicates the underlying potentiality and challenges within the field.

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“…Subjection of C2-symmetricalb is(indole)-1,3-diynes 302 under the previously optimized reaction conditions, 58 %y ield of 2,3'-diiodo-9 H,9'H-1,4'-bicarbazole 303 was obtained.C oupling of bis(iodocarbazoles) with appropriate boronic acid derivativities under Suzuki-Miyaura conditions delivered the desired [7]helicenocarbazoles 304 (Scheme77). [90] argyl amines ( Figure 6) which belong to the class of compounds with high material and medicinal importance.S ince its discovery, these functionalized alkynes have been utilized for the synthesis of numerousc arbo-and heterocycles and natural products.T his sectiond eals with the recent transformationso f heteroarene-tetheredN -protected/unprotected propargylamines.…”

Section: Scheme73mentioning

confidence: 99%

“…Coupling of bis(iodocarbazoles) with appropriate boronic acid derivativities under Suzuki–Miyaura conditions delivered the desired [7]helicenocarbazoles 304 (Scheme 77). [90] …”

Section: Metamorphosis Of Heteroarene‐tethered 2‐alkynyl Alcohols Andmentioning

confidence: 99%

Heteroarene‐tethered Functionalized Alkyne Metamorphosis

Bag

Sawant

2020

Chemistry A European J

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Heteroarene-tethered functionalized alkynes are multipotents ynthons in organic chemistry.T his detailed Review described herein offers at horough discussion of the metamorphosis of heteroarene-tethered functionalized alkynes, an area which has earned much attention over the past decade in the straightforward synthesis of architecturally complex heterocyclics caffolds in atom and step economic manner.D epending upon the variety of functionalized al-kynes, this Review is divided into multiple sections. Amongst the vast array of synthetic transformations covered, dearomatizings pirocyclizations and cascades pirocyclization/rearrangementa re of great interest. Synthetic transformations involving the heteroarene-tethered functionalized alkynes with scope, challenges, limitations, mechanism, their application in the total synthesis of natural products and future perceptionsa re surveyed. [a] D. Bag, Prof.

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A Facile Synthesis of Blue Luminescent [7]Helicenocarbazoles Based on Gold‐Catalyzed Rearrangement‐Iodonium Migration and Suzuki–Miyaura Benzannulation Reactions

Abstract: New azahelicenes having interesting photophysical properties have been prepared in a four-step sequence. These [7]helicenocarbazoles are efficient blue luminophores, demonstrating the utility of gold catalysis in the preparation of advanced materials.

Cited by 11 publications

References 32 publications

Homogeneous and Heterogeneous Gold Catalysis for Materials Science

Homogeneous and Heterogeneous Gold Catalysis for Materials Science

Transition‐Metal‐Catalyzed Carbohalogenative 1,2‐Difunctionalization of C−C Multiple Bonds

Heteroarene‐tethered Functionalized Alkyne Metamorphosis

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