Palladium-Catalyzed Modular Synthesis of Enantioenriched Pyridohelicenes through Double Imidoylative Cyclization

Article Chemistry, Multidisciplinary

Synthesis of (Di)thiahelicenes and Dithiophenohelicenes by [2+2+2] Cycloisomerization of Alkynes

Ondrej Palata et al.

Summary: A series of inherently chiral di- and tetrathiahelicenes/dithiophenohelicenes were synthesized and their structural and physicochemical properties were studied and compared with other related compounds.

HELVETICA CHIMICA ACTA (2022)

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Article Chemistry, Multidisciplinary

A New Saddle-Shaped Aza Analog of Tetraphenylene: Atroposelective Synthesis and Application as a Chiral Acylating Reagent

Yu Luo et al.

Summary: A unique saddle-shaped bridged biaryl, (Z)-7-Aryl- 5-acyldibenzo[e, g][1,4]diazocin-6(5H)-one, was synthesized for the first time. The synthesis method and its application as a recyclable acylating reagent were discussed, highlighting its significance.

CCS CHEMISTRY (2022)

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Review Chemistry, Multidisciplinary

Carbo[n]helicenes Restricted to Enantiomerize: An Insight into the Design Process of Configurationally Stable Functional Chiral PAHs

Prince Ravat

Summary: The interconversion of enantiomers is a key stereodynamic feature of carbo[n]helicenes, with the Gibbs activation energy determining their configurational stability. This minireview provides an overview of the mechanism, recent developments, and factors affecting the enantiomerization of [n]helicenes, aiming to accelerate the design process of configurationally stable functional chiral molecules based on helicene substructures. Additionally, misconceptions and irregularities in the recent literature on terms such as racemization and enantiomerization, as well as the calculation of activation parameters for [n]helicenes and related compounds, are addressed.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

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Review Chemistry, Multidisciplinary

Chiroptical Properties of Symmetric Double, Triple, and Multiple Helicenes

Tadashi Mori

Summary: This review focuses on the chiroptical properties of multiple helicenes, with an emphasis on the impact of the arrangement of multiple helices on the chiroptical responses. Although the number of multiple helicenes reported is limited, insights into the design principle for advanced chiroptical materials through the proper arrangement of multiple helices are provided.

CHEMICAL REVIEWS (2021)

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Article Chemistry, Multidisciplinary

Enantioselective Synthesis of Azoniahelicenes by Rh-Catalyzed C-H Annulation with Alkynes

Qiang Wang et al.

Summary: This study reveals a rhodium(III)-catalyzed enantioselective C-H activation/annulation process for the synthesis of chiral azoniahelicenes with high yields and enantioselectivity. Mechanistic studies suggest that C-H bond cleavage may be the turnover-limiting step.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Organic

Ring-Expansion Strategy for α-Aryl Azahelicene Construction: Building Blocks for Optoelectronic Materials

Jia Feng et al.

Summary: This research reports a method of rapid synthesis of alpha-aryl azahelicenes through C-C bond cleavage of helical 9H-fluoren-9-ols, providing an excellent opportunity to further adjust the photoluminescence properties through the introduction of new aryl rings and pyridine moieties. The novel alpha-aryl azahelicenes exhibit high circularly polarized luminescence efficiencies and brightness, indicating a potential application as chiral emitters.

ORGANIC LETTERS (2021)

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Article Chemistry, Multidisciplinary

Palladium-Catalyzed Atroposelective Coupling-Cyclization of 2-Isocyanobenzamides to Construct Axially Chiral 2-Aryl- and 2,3-Diarylquinazolinones

Fan Teng et al.

Summary: A palladium-catalyzed imidoylative cycloamidation of N-alkyl-2-isocyanobenzamides with 2,6-disubstituted aryl iodides has been developed to afford unprecedented axially chiral 2-arylquinazolinones with good yields and atroposelectivities. The coupling-cyclization process allows for the sequential formation of the biaryl linkage and the heteroaromatic ring in one step. When N-(2,4dimethoxyphenyl)-2-isocyanobenzamide is used as a substrate, 2,3-diarylquinazolinones containing two stereogenic axes are produced with moderate diastereoselectivity and good enantioselectivities.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Review Chemistry, Multidisciplinary

Frontiers in circularly polarized luminescence: molecular design, self-assembly, nanomaterials, and applications

Zhong-Liang Gong et al.

Summary: Research in circularly polarized luminescence has recently gained widespread interest, focusing on the development of chiral materials with high luminescence efficiency and dissymmetry factors, as well as their applications in optoelectronic devices. This review summarizes the latest advancements in this field, including the development of various chiral emissive materials and the utilization of these materials in organic light-emitting devices and other applications.

SCIENCE CHINA-CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Rhodium-Catalyzed Enantioselective Synthesis, Structures, and Properties of Single and Double Azahelicene-Like Molecules

Kyoichi Hanada et al.

Summary: Enantioselective synthesis of aza[6] and [7]helicene-like molecules was achieved through a specific catalytic system, yielding a highly enantioselective S-shaped double aza[6]helicene-like molecule with good fluorescent quantum yields and chiroptical responses under various conditions.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

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Article Chemistry, Physical

Helical Bisphosphinites in Asymmetric Tsuji-Trost Allylation: a Remarkable P:Pd Ratio Effect

Caleb Medena et al.

Summary: This study reveals the significant role of a chiral bis-phosphorylated-helical ligand in the palladium-catalyzed Tsuji-Trost allylation. It was found that the (R) and (S) isomeric products can be selectively formed based on the amount of ligand introduced. Analysis through P-31 NMR spectroscopy, X-Ray diffraction, and DFT calculations shed light on the mechanism behind the role of organometallic species involved.

CHEMCATCHEM (2021)

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Article Chemistry, Inorganic & Nuclear

Enantioenriched Ruthenium-Tris-Bipyridine Complexes Bearing One Helical Bipyridine Ligand: Access to Fused Multihelicenic Systems and Chiroptical Redox Switches

Martin Kos et al.

Summary: This study describes the synthesis, photophysical, and chiroptical properties of novel aza[n]helicenes substituted with 2-pyridyl groups. The prepared compounds were coordinated to Ru(bipy)(2)(2+) units to form helical architectures, and their topology and stereochemistry were studied in detail using X-ray crystallography. Interestingly, the coordination to ruthenium(II) allowed for the preparation of fused multihelical systems incorporating aza- and ruthena-helicenes with redox-triggered chiroptical switching activity.

INORGANIC CHEMISTRY (2021)

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Article Chemistry, Physical

Enantioselective Construction of 1H-Isoindoles Containing Tri- and Difluoromethylated Quaternary Stereogenic Centers via Palladium-Catalyzed C-H Bond Imidoylation

Jian Wang et al.

Summary: An intermolecular enantioselective synthesis of 1H-isoindoles containing tri- and difluoromethylated quaternary stereogenic centers has been developed through a palladium-catalyzed desymmetric C-H bond imidoylation. The fluoroalkyl group was found to be crucial in both the stereochemistry and reaction efficiency. Additionally, an allene insertion cascade was realized, providing a rapid access to diverse C1-tethered bis-heterocyclic scaffolds with good yields and high enantioselectivities under mild conditions with low catalyst loadings.

ACS CATALYSIS (2021)

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Review Chemistry, Multidisciplinary

Helically Chiral Aromatics: The Synthesis of Helicenes by [2+2+2] Cycloisomerization of π-Electron Systems

Irena G. Stara et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

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Article Chemistry, Multidisciplinary

Enantioselective Synthesis of 1,12-Disubstituted [4]Helicenes

Thierry Hartung et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Multidisciplinary

Rhodium-Catalyzed Highly Diastereo- and Enantioselective Synthesis of a Configurationally Stable S-Shaped Double Helicene-Like Molecule

Suzuka Kinoshita et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Multidisciplinary

Enantioselective Synthesis of Triple Helicenes by Cross-Cyclotrimerization of a Helicenyl Aryne and Alkynes via Dynamic Kinetic Resolution

Ayaka Yubuta et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Multidisciplinary

Enantioselective Synthesis of 1-Aryl Benzo[5]helicenes Using BINOL-Derived Cationic Phosphonites as Ancillary Ligands

Pablo Redero et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Organic

Pd-Catalyzed Domino Imidoylation/Heck/C(sp2)-H Cyclization: Isocyanide Relay Strategy toward Tricyclic-Fused Heterocycles Containing an All-Carbon Quaternary Center

Fan Teng et al.

ORGANIC LETTERS (2020)

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Review Chemistry, Multidisciplinary

Helicene Radicals: Molecules Bearing a Combination of Helical Chirality and Unpaired Electron Spin

Fumito Tani et al.

CHEMPLUSCHEM (2020)

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Article Chemistry, Organic

Pd-Catalyzed C(sp2)-H Imidoylative Annulation: A General Approach To Construct Dibenzoox(di)azepines

Weiming Hu et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

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Review Chemistry, Multidisciplinary

Enantioenriched Helicenes and Helicenoids Containing Main-Group Elements (B, Si, N, P)

Kais Dhbaibi et al.

CHEMICAL REVIEWS (2019)

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Article Chemistry, Multidisciplinary

Enantioselective Control of Both Helical and Axial Stereogenic Elements though an Organocatalytic Approach

Shiqi Jia et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Organic

Triarylborane-based [5]Helicenes with Full-Color Circularly Polarized Luminescence

Zheng-Hua Zhao et al.

ORGANIC LETTERS (2019)

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Article Chemistry, Applied

Selective C-H or N-H Imidoylative Annulation of 2-(2-Isocyanophenyl)-1H-indoles Leading to Diverse Indole-fused Scaffolds

Fan Teng et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

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Review Chemistry, Multidisciplinary

Advances in helicene derivatives with circularly polarized luminescence

Wen-Long Zhao et al.

CHEMICAL COMMUNICATIONS (2019)

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Article Chemistry, Organic

Asymmetric Synthesis of Nonracemic 2-Amino[6]helicenes and Their Self-Assembly into Langmuir Films

Manfred Karras et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

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Article Chemistry, Organic

Enantioselective Synthesis of Planar Chiral Pyridoferrocenes via Palladium-Catalyzed Imidoylative Cyclization Reactions

Shuang Luo et al.

ORGANIC LETTERS (2018)

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Article Chemistry, Multidisciplinary

Enantioselective Synthesis of [6]Carbohelicenes

Elisa Gonzalez-Fernandez et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

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Article Chemistry, Organic

Helically Chiral 1-Sulfur-Functionalized [6]Helicene: Synthesis, Optical Resolution, and Functionalization

Tetsuya Tsujihara et al.

ORGANIC LETTERS (2017)

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Article Chemistry, Organic

Palladium-Catalyzed Imidoylative Cyclization of Tryptophan-Derived Isocyanides: Access to β-Carbolines

Shi Tang et al.

ORGANIC LETTERS (2017)

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Article Chemistry, Physical

Palladium-Catalyzed Enantioselective C(sp2)-H lmidoylation by Desymmetrization

Jian Wang et al.

ACS CATALYSIS (2017)

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Article Chemistry, Multidisciplinary

Gold-Catalyzed Enantioselective Synthesis, Crystal Structure, and Photophysical/Chiroptical Properties of Aza[10]helicenes

Maya Tanaka et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

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Article Chemistry, Physical

Controlled Excited-State Dynamics and Enhanced Fluorescence Property of Tetrasulfone[9]helicene by a Simple Synthetic Process

Yuki Yamamoto et al.

JOURNAL OF PHYSICAL CHEMISTRY C (2016)

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Article Chemistry, Organic

Palladium-Catalyzed Intramolecular C(sp2)-H Imidoylation for the Synthesis of Six-Membered N-Heterocycles

Jing Li et al.

JOURNAL OF ORGANIC CHEMISTRY (2015)

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Article Chemistry, Multidisciplinary

Ligand-Receptor Interaction Catalyzes the Aggregation of Small Molecules To Induce Cell Necroptosis

Junfeng Shi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

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Article Chemistry, Multidisciplinary

Enantioselective Synthesis and Enhanced Circularly Polarized Luminescence of S-Shaped Double Azahelicenes

Kyosuke Nakamura et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Review Chemistry, Multidisciplinary

Helicene-based transition metal complexes: synthesis, properties and applications

Nidal Saleh et al.

CHEMICAL SCIENCE (2014)

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Article Chemistry, Multidisciplinary

Rapid Access to Dibenzohelicenes and their Functionalized Derivatives

Andrej Jancarik et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

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Review Chemistry, Multidisciplinary

Palladium-Catalyzed Migratory Insertion of Isocyanides: An Emerging Platform in Cross-Coupling Chemistry

Tjostil Vlaar et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

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Article Chemistry, Multidisciplinary

Applications of Helical-Chiral Pyridines as Organocatalysts in Asymmetric Synthesis

Zhili Peng et al.

CHEMICAL RECORD (2013)

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Review Chemistry, Multidisciplinary

Recent advances in isocyanide insertion chemistry

Guanyinsheng Qiu et al.

CHEMICAL SOCIETY REVIEWS (2013)

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Review Chemistry, Multidisciplinary

Unravelling the labyrinth of palladium-catalysed reactions involving isocyanides

Stuart Lang

CHEMICAL SOCIETY REVIEWS (2013)

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Review Chemistry, Multidisciplinary

One hundred years of helicene chemistry. Part 3: applications and properties of carbohelicenes

Marc Gingras

CHEMICAL SOCIETY REVIEWS (2013)

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Review Chemistry, Multidisciplinary

One hundred years of helicene chemistry. Part 1: non-stereoselective syntheses of carbohelicenes

Marc Gingras

CHEMICAL SOCIETY REVIEWS (2013)

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Review Chemistry, Multidisciplinary

One hundred years of helicene chemistry. Part 2: stereoselective syntheses and chiral separations of carbohelicenes

Marc Gingras et al.

CHEMICAL SOCIETY REVIEWS (2013)

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Article Chemistry, Inorganic & Nuclear

Chiral cobalt(I) and nickel(0) complexes in the synthesis of nonracemic helicenes through the enantioselective [2+2+2] cyclotrimerisation of alkynes

Barbara Heller et al.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2013)

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Article Chemistry, Organic

A Scalable and Expedient Route to 1-Aza[6]helicene Derivatives and Its Subsequent Application to a Chiral-Relay Asymmetric Strategy

Marko Weimar et al.

ORGANIC LETTERS (2013)

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Article Chemistry, Multidisciplinary

Highly enantioselective synthesis of silahelicenes using Ir-catalyzed [2+2+2] cycloaddition

Takanori Shibata et al.

CHEMICAL COMMUNICATIONS (2012)

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Review Chemistry, Multidisciplinary

Helicenes: Synthesis and Applications

Yun Shen et al.

CHEMICAL REVIEWS (2012)

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Rhodium-Catalyzed Enantioselective Synthesis, Crystal Structures, and Photophysical Properties of Helically Chiral 1,1′-Bitriphenylenes

Yayoi Sawada et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

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Article Chemistry, Multidisciplinary

A Chiral Wedge Molecule Inhibits Telomerase Activity

Ken-ichi Shinohara et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

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Article Chemistry, Organic

Asymmetric Synthesis and Photophysical Properties of Benzopyrano- or Naphthopyrano-Fused Helical Phosphafluorenes

Naahiro Fukawa et al.

ORGANIC LETTERS (2010)

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Article Chemistry, Organic

Azahelicenes and other similar tri and tetracyclic helical molecules

Florea Dumitrascu et al.

ARKIVOC (2010)

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Enantioselective Synthesis of [7]Helicene: Dramatic Effects of Olefin Additives and Aromatic Solvents in Asymmetric Olefin Metathesis

Alain Grandbois et al.

CHEMISTRY-A EUROPEAN JOURNAL (2008)

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Article Chemistry, Multidisciplinary

Asymmetric reductive coupling of dienes and aldehydes catalyzed by nickel complexes of spiro phosphoramidites: Highly enantioselective synthesis of chiral bishomoallylic alcohols

Yun Yang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

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Article Chemistry, Applied

Asymmetric catalysis in the [2+2+2] cycloaddition of arynes and alkynes:: Enantioselective synthesis of a pentahelicene

Jorge Caeiro et al.

ADVANCED SYNTHESIS & CATALYSIS (2006)

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Article Chemistry, Inorganic & Nuclear

Enantioselective synthesis induced by tetrathia-[7]-helicenes in conjunction with asymmetric autocatalysis

Tsuneomi Kawasaki et al.

TETRAHEDRON-ASYMMETRY (2006)

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Article Chemistry, Organic

Towards the stereoselective synthesis of inherently chiral pseudorotaxanes

P Mobian et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2006)

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Palladium-Catalyzed Modular Synthesis of Enantioenriched Pyridohelicenes through Double Imidoylative Cyclization

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