4.8 Article

Ligand-Controlled Regiodivergence in Nickel-Catalyzed Vinylcyclopropane Rearrangement

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Article Chemistry, Multidisciplinary

Donor-Acceptor Cyclopropanes: Activation Enabled by a Single, Vinylogous Acceptor

Nils L. Ahlburg et al.

Summary: A novel class of highly activated donor-acceptor cyclopropanes with a single vinylogous acceptor is presented. These moieties undergo cycloaddition reactions with various substrates to form carbo- and heterocycles. The stereochemical outcome can be controlled by the choice of catalyst. Mechanistic and kinetic experiments were conducted to explain the catalytic cycle and stereoselectivity.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Article Chemistry, Multidisciplinary

Ligand-Controlled Regiodivergence for Catalytic Stereoselective Semireduction of Allenamides

Mojtaba Hajiloo Shayegan et al.

Summary: This study achieved ligand-controlled regiodivergence for the catalytic semireduction of allenamides with excellent chemo- and stereocontrol.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

Article Chemistry, Multidisciplinary

On the Origin of Rh-Catalyzed Selective Ring-Opening Amidation of Substituted Cyclopropanols to Access β2-Amino Ketones

Minhan Lee et al.

Summary: A highly efficient Rh-catalyzed reaction for the selective synthesis of beta(2)-amino ketones is reported, showcasing its significance in the development of new pharmaceuticals and peptidomimetics.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Multidisciplinary

Ni-Catalyzed Divergent Synthesis of 2-Benzazepine Derivatives via Tunable Cyclization and 1,4-Acyl Transfer Triggered by Amide N-C Bond Cleavage

Yuanyuan Ping et al.

Summary: Ligand-directed divergent synthesis is a strategy that can transform common starting materials into distinct molecular scaffolds. This strategy enables the rapid construction of structurally rich collection of small molecules for biological evaluation and reveals novel modes of catalytic transformation, representing one of the most sought-after challenges in synthetic chemistry.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Multidisciplinary

Confronting the Challenging Asymmetric Carbonyl 1,2-AdditionUsing Vinyl Heteroarene Pronucleophiles: Ligand-ControlledRegiodivergent Processes through a Dearomatized Allyl-Cu Species

Yuyang Dong et al.

Summary: This article introduces a CuH-catalyzed selective reductive coupling reaction of vinyl heteroarenes with aldehydes and ketones. The selectivity of the reaction is controlled by the choice of the ancillary ligand. This method shows excellent selectivity, tolerates various functional groups and heterocycles, and provides a direct route to functionalized saturated heterocyclic structures.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Physical

Copper-Catalyzed Yne-Allylic Substitutions Using Stabilized Nucleophiles

Shengtong Niu et al.

Summary: In this work, a general protocol for copper-catalyzed allylic substitutions using stable soft nucleophiles has been developed, resulting in the synthesis of highly selective functionalized 1,3- and 1,4-enynes. Mechanistic studies propose a copper acetylide-bonded allylic cation as the key intermediate, featuring an outer-sphere nucleophilic attack. The demonstrated diversified reactivities in this study will inspire further exploration.

ACS CATALYSIS (2022)

Article Chemistry, Physical

Pd/NHC-Controlled Regiodivergent Defluorinative Allylation of gem-Difluorocyclopropanes with Allylboronates

Leiyang Lv et al.

Summary: This study reports a catalytic method for controlling the selectivity of reactions, allowing access to diverse fluorinated 1,5-dienes from the same starting materials. Density functional theory calculations also revealed a ligand design for switching selectivity. This ligand-controlled approach is important for late-stage modification of complex molecules.

ACS CATALYSIS (2022)

Article Chemistry, Multidisciplinary

Ligand-Controlled Cobalt-Catalyzed Regiodivergent Alkyne Hydroalkylation

Yan Li et al.

Summary: In this study, a ligand-controlled cobalt-catalyzed regiodivergent alkyne hydroalkylation method is reported, which can generate different isomers of an alkene from the same alkyne starting material. The method provides reliable and predictable protocols with high selectivity for the synthesis of specific alkenes.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Organic

Connect Four: Tetraarylated Dihydropentalenes and Triarylated Monocyclic Pentafulvenes from Cyclopentadienes and Enones

Niko A. Jenek et al.

Summary: We report a method for the Michael annulation of dihydropentalenes with α,β-unsaturated ketones, and successfully synthesized various novel pentalenide ligands. The properties of the products vary depending on the substitution patterns and molecular polarization.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Review Chemistry, Multidisciplinary

Selective Carbon-Carbon Bond Cleavage of Cyclopropylamine Derivatives

Olga O. Sokolova et al.

Summary: This review summarizes synthetic developments reported from 1987 to 2019 that exploit C-C single bond cleavage of cyclopropylamine-based systems. The synthetic and mechanistic aspects of key methodologies are highlighted, and examples where aminocyclopropanes are exploited as key intermediates in multistep synthesis are also discussed. The review encompasses cases where aminocyclopropanes participate in polar reactions, pericyclic processes, radical-based reactions, and C-C bond activations.

CHEMICAL REVIEWS (2021)

Review Chemistry, Multidisciplinary

Transition Metal-Catalyzed Selective Carbon-Carbon Bond Cleavage of Vinylcyclopropanes in Cycloaddition Reactions

Jianhua Wang et al.

Summary: This review focuses on transition metal-catalyzed methodologies and applications involving the cleavage of C-C bonds in vinylcyclopropanes (VCPs) for cycloaddition and related addition reactions. It discusses the properties of activated and nonactivated VCPs, transition metal-catalyzed cycloadditions, and addition reactions, as well as challenges and potential opportunities in the field.

CHEMICAL REVIEWS (2021)

Article Chemistry, Multidisciplinary

A Dinickel Catalyzed Cyclopropanation without the Formation of a Metal Carbene Intermediate

Arnab K. Maity et al.

Summary: (NDI)Ni-2 catalysts promote cyclopropanation reactions of 1,3-dienes by coupling with (Me3Si)CHN2. Mechanistic studies and DFT models suggest an alternative reaction mechanism involving Ni-2 mediated coupling and N-2 extrusion for generating cyclopropane products, explaining the experimental observations.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Migratory Hydrocyanation of Internal Alkenes: Unexpected Diastereomeric-Ligand-Controlled Regiodivergence

Jihui Gao et al.

Summary: A regiodivergent nickel-catalyzed hydrocyanation of a broad range of internal alkenes with high regioselectivities is reported, achieving either linear or branched nitriles with good yields. DFT calculations showed that the catalyst architecture plays a crucial role in determining regioselectivity by modulating electronic and steric interactions. Additionally, moderate enantioselectivities were observed in the production of branched nitriles.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Review Chemistry, Multidisciplinary

Cleavage of Carbon-Carbon σ-Bonds of Four-Membered Rings

Masahiro Murakami et al.

Summary: This article reviews synthetic transformations involving the cleavage of a carbon-carbon bond of a four-membered ring from 2011 to 2019, with a particular focus on progress in catalytic reactions such as oxidative addition and beta-carbon elimination, as well as the increasing attention on beta-scission of radical intermediates. Additionally, Lewis acid-mediated and thermally induced ring-opening of cyclobutanone derivatives have garnered renewed interest, demonstrating the unique synthetic potentials of structurally strained four-membered ring compounds for constructing organic skeletons.

CHEMICAL REVIEWS (2021)

Article Chemistry, Multidisciplinary

Ligand coordination- and dissociation-induced divergent allylic alkylations using alkynes

Yuan Huang et al.

Summary: In nickel/copper-catalyzed reactions, different ligands can result in different substrate coupling reactions, which is a rare phenomenon in multi-substrate coordination and coupling.
Article Chemistry, Organic

Ligand-Controlled Regiodivergent Nickel-Catalyzed Hydrocyanation of Silyl-Substituted 1,3-Diynes

Feilong Sun et al.

Summary: A regiodivergent nickel-catalyzed hydrocyanation of 1-aryl-4-silyl-1,3-diynes is reported, where appropriate ligands result in high yields and regioselectivities of two different enynyl nitriles. DFT calculations show that different ligands lead to diverse alkyne insertion modes, impacting the regioselectivity. The synthetic value of cyano-containing 1,3-enynes is demonstrated through downstream transformations.

ORGANIC LETTERS (2021)

Article Chemistry, Multidisciplinary

Ni-Catalyzed Ligand-Controlled Regiodivergent Reductive Dicarbofunctionalization of Alkenes

Qi Pan et al.

Summary: This study presents a catalyst-controlled dicarbofunctionalization of alkenes for the synthesis of five- and six-membered benzo-fused lactams bearing all-carbon quaternary centers. Different regioselectivity patterns can be achieved by using chiral bidentate ligands, resulting in high yields and excellent enantioselectivities. The synthetic value of this regiodivergent protocol is demonstrated by the preparation of biologically relevant molecules and structural scaffolds.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Organic

Enantioselective Cyclobutenylation of Olefins Using N-Sulfonyl-1,2,3-Triazoles as Vicinal Dicarbene Equivalents

Sajan C. Patel et al.

Summary: The study presents a method for the synthesis of cyclobutenes from olefins through a complex reaction pathway, achieving high yields and enantioenrichment.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Transition-Metal-Catalyzed Hydroxylation Reaction of Aryl Halide for the Synthesis of Phenols

L. Xue et al.

Summary: This article briefly discusses recent advances in catalytic hydroxylation reactions for the synthesis of phenols, with a focus on the efficient use of water as a hydroxide reagent. This methodology allows for the synthesis of diverse phenols and enables the hydroxylation of multifunctional pharmaceutically relevant aryl halides.

SYNLETT (2021)

Article Chemistry, Multidisciplinary

Ligand-Controlled Regiodivergence in Nickel-Catalyzed Hydroarylation and Hydroalkenylation of Alkenyl Carboxylic Acids

Zi-Qi Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Ni-Catalyzed Regiodivergent and Stereoselective Hydroalkylation of Acyclic Branched Dienes with Unstabilized C(sp3) Nucleophiles

Wen Shao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Multidisciplinary Sciences

E-Olefins through intramolecular radical relocation

Ajoy Kapat et al.

SCIENCE (2019)

Review Chemistry, Multidisciplinary

Metal-catalyzed regiodivergent organic reactions

Carmen Najera et al.

CHEMICAL SOCIETY REVIEWS (2019)

Article Chemistry, Multidisciplinary

Bronsted Acid-Catalyzed Carbonyl-Olefin Metathesis inside a Self-Assembled Supramolecular Host

Lorenzo Catti et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Inorganic & Nuclear

Dinuclear Pathways for the Activation of Strained Three-Membered Rings

Heather R. Rounds et al.

ORGANOMETALLICS (2018)

Article Chemistry, Multidisciplinary

Regiodivergent Catalysis: A Powerful Tool for Selective Catalysis

Nico Funken et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

Review Chemistry, Organic

Synthetic applications of vinyl cyclopropane opening

Marta Meazza et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2017)

Article Multidisciplinary Sciences

Iron(III)-catalysed carbonyl-olefin metathesis

Jacob R. Ludwig et al.

NATURE (2016)

Review Chemistry, Multidisciplinary

Catalytic C-C Bond Activations via Oxidative Addition to Transition Metals

Laetitia Souillart et al.

CHEMICAL REVIEWS (2015)

Article Biochemistry & Molecular Biology

A new approach towards the synthesis of drospirenone and steroidal spirolactones

Bindu Santhamma et al.

STEROIDS (2015)

Review Chemistry, Multidisciplinary

A New Golden Age for Donor-Acceptor Cyclopropanes

Tobias F. Schneider et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

β-Carbon activation of saturated carboxylic esters through N-heterocyclic carbene organocatalysis

Zhenqian Fu et al.

NATURE CHEMISTRY (2013)

Article Chemistry, Inorganic & Nuclear

Enhanced Activity of [Ni(NHC)CpCl] Complexes in Arylamination Catalysis

Anthony R. Martin et al.

ORGANOMETALLICS (2013)

Article Chemistry, Inorganic & Nuclear

IPr* an easily accessible highly hindered N-heterocyclic carbene

Guillaume Berthon-Gelloz et al.

DALTON TRANSACTIONS (2010)

Article Chemistry, Organic

Mechanism of the Ni(0)-Catalyzed Vinylcyclopropane-Cyclopentene Rearrangement

Selina C. Wang et al.

JOURNAL OF ORGANIC CHEMISTRY (2009)

Article Chemistry, Multidisciplinary

Rhodium-Catalyzed Enantioselective Cyclopropanation of Olefins with N-Sulfonyl 1,2,3-Triazoles

Stepan Chuprakov et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

Article Chemistry, Multidisciplinary

Synthesis of Cyclobutenes by Highly Selective Transition-Metal-Catalyzed Ring Expansion of Cyclopropanes

Huadong Xu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

Article Chemistry, Inorganic & Nuclear

Metal promoted vinylcyclopropane-cyclopentene rearrangements: Reactions ripe for mechanism-based catalyst design

Selina C. Wang et al.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2006)

Article Chemistry, Multidisciplinary

Highly active nickel catalysts for the isomerization of unactivated vinyl cyclopropanes to cyclopentenes

G Zuo et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2004)