4.8 Article

Gold(I)-Catalyzed Regioselective Hydroarylation of Propiolic Acid with Arylboronic Acids

Related references

Note: Only part of the references are listed.
Article Chemistry, Physical

Hydrogen Bond Donor and Unbalanced Ion Pair Promoter-Assisted Gold-Catalyzed Carbon-Oxygen Cross-Coupling of (Hetero)aryl Iodides with Alcohols

Guifang Chen et al.

Summary: We developed an efficient gold-catalyzed C-O cross-coupling reaction of (hetero)aryl iodides with primary and secondary alcohols via an AuI-AuIII catalytic cycle. This protocol exhibited moisture/air insensitivity, simple operation, and excellent functional group tolerance. Good yields were obtained regardless of steric hindrance and electronic factor, and the chirality of chiral alcohol starting materials could be preserved. Our protocol also worked well for both intermolecular and intramolecular couplings. The RuPhos ligand was used as a catalyst for gold-catalyzed cross-couplings. An unbalanced ion pair promoter and hydrogen bond donor solvent might be crucial in this transformation.

ACS CATALYSIS (2023)

Article Chemistry, Multidisciplinary

Gold-Catalyzed Heck Reaction

Vivek W. Bhoyare et al.

Summary: In this study, we present a ligand-enabled gold (Au) catalyzed Heck reaction using Au(I)/Au(III) redox catalysis. For the first time in gold chemistry, essential organometallic steps such as migratory insertion and s-hydride elimination have been achieved in a catalytic manner. This methodology not only overcomes the limitations of previous transition metal-catalyzed Heck reactions, such as the need for specialized substrates and the formation of a mixture of regioisomeric products due to undesirable chain-walking, but also provides complementary regioselectivity compared to other transition metal catalysis.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

Article Chemistry, Organic

Gold-Catalyzed Aryl-Alkenylation of Alkenes

Anil Kumar et al.

Summary: Here, we describe the gold-catalyzed aryl-alkenylation of unactivated alkenes with alkenyl iodides and bromides using ligand-enabled gold redox catalysis. Unlike traditional transition metal catalysis like Pd, Ni, Cu, etc., this methodology operates through the pi-activation pathway instead of the migratory insertion pathway. Mechanistic insights have been provided through detailed investigations such as 31P NMR, deuterium labeling, and HRMS studies.

ORGANIC LETTERS (2023)

Article Chemistry, Multidisciplinary

Gold (I/III)-Catalyzed Trifluoromethylthiolation and Trifluoromethylselenolation of Organohalides

Sagar R. Mudshinge et al.

Summary: The first C-SCF3/SeCF3 cross-coupling reactions using gold redox catalysis are reported. The new method enables the one-stop synthesis of aryl/alkenyl/alkynyl trifluoromethylthio- and selenoethers, with a broad substrate scope. It is scalable and can be applied to late-stage functionalization of bioactive molecules.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Review Biochemistry & Molecular Biology

Recent Advances in Gold(I)-Catalyzed Approaches to Three-Type Small-Molecule Scaffolds via Arylalkyne Activation

Lu Yang et al.

Summary: This paper summarizes the recent advances in the construction of small-molecule scaffolds through gold-catalyzed cyclization of arylalkyne derivatives within the last decade. Gold catalysts have the advantages of water and oxygen resistance, and can achieve the rapid construction of multiple chemical bonds and ring systems.

MOLECULES (2022)

Review Chemistry, Multidisciplinary

Gold-Catalyzed Synthesis of Spirocycles: Recent Advances

Somnath Ganguly et al.

Summary: This review article provides an overview of gold-catalyzed reactions for the formation of spirocycles from various substrates, including methodologies, applications, and mechanistic insights.

CHEMISTRYSELECT (2022)

Review Chemistry, Organic

Gold-catalyzed hydroarylation reactions: a comprehensive overview

Tapas Ghosh et al.

Summary: Gold-catalyzed hydroarylation is a cost-effective and efficient method for incorporating unsaturated moieties into aromatic substrates by directly functionalizing C-H bonds. It offers a synthetic strategy with fewer reaction steps.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Review Chemistry, Multidisciplinary

Construction of Medium-Sized Rings by Gold Catalysis

Ronald L. Reyes et al.

Summary: This review focuses on methodologies for constructing medium-sized rings using gold catalysis, particularly emphasizing the pathway, precursor selection, catalyst choice, and mechanistic attributes. Gold-mediated cyclization reactions show significant potential in building 7-membered rings and medium-sized (8-11-membered) ring structures.

CHEMICAL REVIEWS (2021)

Review Chemistry, Multidisciplinary

Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes

Dominic Campeau et al.

Summary: This review discusses the gold-catalyzed reactions of specially activated alkynes, allenes, and alkenes, highlighting their unique reactivities and applications within different substrate categories.

CHEMICAL REVIEWS (2021)

Review Chemistry, Multidisciplinary

Light in Gold Catalysis

Sina Witzel et al.

Summary: Gold photocatalysis in gold-catalyzed reactions offers unique advantages, allowing for valence change of the gold center through electron transfer and radical addition without the need for stoichiometric sacrificial oxidants. The compatibility of radicals with gold catalysts enables a variety of important organic transformations, including redox-neutral C-C and C-X coupling, C-H activation, and formal radical-radical cross-coupling.

CHEMICAL REVIEWS (2021)

Review Chemistry, Multidisciplinary

Optimization of Catalysts and Conditions in Gold(I) Catalysis-Counterion and Additive Effects

Zhichao Lu et al.

Summary: Gold catalysis has been a significant breakthrough in organic synthesis due to its tunable nature, unique properties, and mild reaction conditions. Despite its popularity, gold-catalyzed reactions still face limitations such as low turnover numbers. Optimizing catalysts and reaction conditions may enhance the efficiency of gold-catalyzed reactions. This review focuses on examples of counterion or additive-regulated gold catalysis from a mechanistic perspective, highlighting the impact of physical properties on gold catalyst reactivity.

CHEMICAL REVIEWS (2021)

Article Chemistry, Organic

Gold(I)-Catalyzed Intramolecular Hydroarylation of Phenol-Derived Propiolates and Certain Related Ethers as a Route to Selectively Functionalized Coumarins and 2H-Chromenes

Aymeric Cervi et al.

Summary: Efficient methods for the synthesis of phenol-derived propiolates and their Au(I)-catalyzed cyclization to give coumarins have been reported. These methods have been successfully applied to the synthesis of natural products such as ayapin and scoparone.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

A bifunctional ligand enables efficient gold-catalyzed hydroarylation of terminal unactivated propargylic alcohols with heteroareneboronic acids

Shengrong Liao et al.

Summary: In this study, a gold-catalyzed hydroarylation reaction was used to synthesize various terminal aryl-substituted allylic alcohols with moderate to high yields under mild conditions.

TETRAHEDRON (2021)

Review Chemistry, Multidisciplinary

Divergent Gold Catalysis: Unlocking Molecular Diversity through Catalyst Control

Chetan C. Chintawar et al.

Summary: Gold complexes have emerged as powerful catalysts in divergent catalysis, offering unique reactivity profiles due to their tunable soft pi-acidic nature. They not only catalyze reactions of alkynes, alkenes, and allenes effectively, but also provide divergent reaction pathways over other pi-acid catalysts like Ag, Pt, Pd, Rh, Cu, In, Sc, Hg, Zn, etc. Reviews documenting such examples are sporadic, hindering the further development of this burgeoning field, thus necessitating a unified approach like Divergent Gold Catalysis (DGC) to consolidate reports and pave the way for advancement.

CHEMICAL REVIEWS (2021)

Article Chemistry, Multidisciplinary

Azido-Alkynes in Gold(I)-Catalyzed Indole Syntheses

Luca C. Greiner et al.

Summary: The exploitation of nitrogen-functionalized reactive intermediates plays a crucial role in the synthesis of biologically relevant scaffolds, especially those based on gold carbenes. This personal account provides a detailed explanation of the contribution to this sector by developing efficient gold-catalyzed cascade processes based on diversely functionalized azido-alkynes, with challenging cyclizations and their subsequent applications in the synthesis of pharmaceutically relevant scaffolds and natural products being key features of the research.

CHEMICAL RECORD (2021)

Review Chemistry, Multidisciplinary

Optimizing Catalyst and Reaction Conditions in Gold(I) Catalysis-Ligand Development

Alba Collado et al.

Summary: This review examines the use of phosphine and N-heterocyclic carbene complexes of gold(I) as (pre)catalysts in organic synthesis, categorizing them based on ligand structure and focusing on studies that offer quantitative comparisons with existing systems.

CHEMICAL REVIEWS (2021)

Article Biochemistry & Molecular Biology

Synthesis of 4-Substituted-1,2-Dihydroquinolines by Means of Gold-Catalyzed Intramolecular Hydroarylation Reaction of N-Ethoxycarb onyl-N-Propargylanilines

Antonio Arcadi et al.

Summary: An alternative synthetic route to functionalized 1,2-dihydroquinolines using Au(I) catalysis has been reported. This method is based on the use of N-ethoxycarbonyl protected-N-propargylanilines as building blocks, resulting in good yields. The regiodivergent cyclization at the ortho-/para position is achieved through catalyst fine tuning when N-ethoxycarbonyl-N-propargyl-meta-substituted anilines are present.

MOLECULES (2021)

Review Chemistry, Physical

Transition-Metal-Catalyzed Functionalization of Alkynes with Organoboron Reagents: New Trends, Mechanistic Insights, and Applications

Javier Corpas et al.

Summary: This paper discusses the importance of the catalytic functionalization of alkynes with organoboron reagents in synthesis and the latest research progress, including innovations in asymmetric internal alkynes, stereochemistry, and metal migration. It focuses on the practicality, limitations, and challenges for future research of the mechanisms and synthetic methods.

ACS CATALYSIS (2021)

Review Chemistry, Multidisciplinary

Gold-Catalyzed Conversion of Highly Strained Compounds

Deyao Li et al.

Summary: The past decade has been a golden age for homogeneous gold-catalyzed reactions, transforming highly strained molecules into complex molecular architectures through unique electronic properties and catalytic abilities of gold catalysts. These catalysts have shown versatile reaction modes and deepened understanding with the development of various ligands. The evolution of gold catalysis has expanded its application into natural product synthesis and the potentiality of drug discovery, showcasing a magnificent renaissance for this ancient metal.

CHEMICAL REVIEWS (2021)

Review Chemistry, Multidisciplinary

Gold-Catalyzed Synthesis of Small Rings

Mauro Mato et al.

Summary: This review provides a comprehensive summary of major advances and discoveries in gold-catalyzed synthesis of highly strained carbocycles, including cyclopropanes, cyclopropenes, cyclobutanes, cyclobutenes, and their heterocyclic or heterosubstituted analogs, demonstrating the powerful application of homogeneous gold catalysis in constructing small ring compounds.

CHEMICAL REVIEWS (2021)

Article Chemistry, Organic

Recent advances of propiolic acids in organic reactions

Chuanli Chen et al.

TETRAHEDRON LETTERS (2020)

Review Chemistry, Multidisciplinary

Gold-Catalyzed Cross-Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications

A. Nijamudheen et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

Article Chemistry, Organic

Nickel-Catalyzed Directed Hydroarylation of Alkynes with Boronic Acids

Luke E. Hanna et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2019)

Review Chemistry, Multidisciplinary

Boronic acid catalysis

Dennis G. Hall

CHEMICAL SOCIETY REVIEWS (2019)

Article Chemistry, Multidisciplinary

Bifunctional Ligand Enables Efficient Gold-Catalyzed Hydroalkenylation of Propargylic Alcohol

Shengrong Liao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

(P,C) Cyclometalated Gold(III) Complexes: Highly Active Catalysts for the Hydroarylation of Alkynes

Charlie Blons et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Organic

Employing Water as the Hydride Source in Synthesis: A Case Study of Diboron Mediated Alkyne Hydroarylation

Santhosh Rao et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Organic

Gold-Catalyzed Hydroarylation of N-Aryl Alkynamides for the Synthesis of 2-Quinolinones

Taylor Vacala et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Multidisciplinary Sciences

Rational development of catalytic Au(I)/Au(III) arylation involving mild oxidative addition of aryl halides

Abdallah Zeineddine et al.

NATURE COMMUNICATIONS (2017)

Article Chemistry, Multidisciplinary

Ni-Catalyzed regio- and stereoselective addition of arylboronic acids to terminal alkynes with a directing group tether

Madala Hari Babu et al.

CHEMICAL COMMUNICATIONS (2017)

Review Chemistry, Multidisciplinary

Alkenylation of Arenes and Heteroarenes with Alkynes

Vadim P. Boyarskiy et al.

CHEMICAL REVIEWS (2016)

Article Chemistry, Multidisciplinary

Palladium(II)-Catalyzed Regioselective syn-Hydroarylation of Disubstituted Alkynes Using a Removable Directing Group

Zhen Liu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Review Chemistry, Multidisciplinary

Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity

Ruth Dorel et al.

CHEMICAL REVIEWS (2015)

Article Chemistry, Multidisciplinary

AgSbF6-controlled diastereodivergence in alkyne hydroarylation: facile access to Z- and E-alkenyl arenes

Minsik Min et al.

CHEMICAL COMMUNICATIONS (2014)

Review Chemistry, Multidisciplinary

Synthesis of heterocycles via transition-metal-catalyzed hydroarylation of alkynes

Yoshihiko Yamamoto

CHEMICAL SOCIETY REVIEWS (2014)

Article Chemistry, Applied

Rhodium- and Palladium-Catalyzed Hydroarylation of Propargylic Amines with Arylboronic Acids

Antonio Arcadi et al.

ADVANCED SYNTHESIS & CATALYSIS (2010)

Article Chemistry, Organic

Palladium-catalyzed hydroarylation of alkynes with arylboronic acids

Xiaoling Xu et al.

TETRAHEDRON (2010)

Article Chemistry, Multidisciplinary

Cu-catalyzed stereoselective conjugate addition of arylboronic acids to alkynoates

Yoshihiko Yamamoto et al.

CHEMICAL COMMUNICATIONS (2008)

Article Chemistry, Multidisciplinary

Cobalt(II)-Catalyzed Regio- and Stereoselective Hydroarylation of Alkynes with Organoboronic Acids

Pao-Shun Lin et al.

CHEMISTRY-A EUROPEAN JOURNAL (2008)

Review Multidisciplinary Sciences

Relativistic effects in homogeneous gold catalysis

David J. Gorin et al.

NATURE (2007)

Review Chemistry, Multidisciplinary

Catalytic carbophilic activation: Catalysis by platinum and gold pi acids

Alois Fuerstner et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2007)

Article Chemistry, Multidisciplinary

Intramolecular hydroarylation of alkynes catalyzed by platinum or gold:: Mechanism and endo selectivity

C Nevado et al.

CHEMISTRY-A EUROPEAN JOURNAL (2005)

Article Chemistry, Multidisciplinary

The palladium-catalyzed addition of organoboronic acids to alkynes

CH Oh et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2003)