4.8 Article

Triarylborane Catalyzed Carbene Transfer Reactions Using Diazo Precursors

Related references

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

Borane Catalyzed Selective Diazo Cross-Coupling Towards Pyrazoles

Ayan Dasgupta et al.

Summary: This study reported a selective borane-catalyzed cyclization reaction from the combination of two different diazo compounds to produce N-substituted pyrazoles. The reaction employed catalytic amounts of tris(pentafluorophenyl)borane to yield the products in yields ranging from 59% to 80%. Extensive DFT studies were conducted to interpret the mechanism, revealing two tandem catalytic cycles catalyzed by B(C6F5)3.

ADVANCED SYNTHESIS & CATALYSIS (2022)

Review Chemistry, Multidisciplinary

Transition Metal Catalyzed Insertion Reactions with Donor/Donor Carbenes

Benjamin D. Bergstrom et al.

Summary: Donor/donor and donor carbenes, although relatively new in carbene chemistry, have shown exquisite chemo- and stereo-selectivity in various insertion reactions. Recent studies have demonstrated high levels of diastereo- and enantioselectivity with different transition metal catalysts. Methods involving diazo-based carbene precursors and diazo-free metal carbenes have both been successful, providing context for future developments in this emerging field.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

A Diverse Library of Chiral Cyclopropane Scaffolds via Chemoenzymatic Assembly and Diversification of Cyclopropyl Ketones

Donggeon Nam et al.

Summary: This study presents a chemoenzymatic strategy for the stereoselective assembly and diversification of cyclopropyl ketones, a versatile class of functionalized cyclopropanes. By utilizing an engineered variant of sperm whale myoglobin, highly diastereo- and enantioselective construction of these molecules is achieved via olefin cyclopropanation in the presence of a diazoketone carbene donor reagent. The resulting enzymatic products can be further transformed to yield a collection of structurally diverse cyclopropane-containing scaffolds in optically pure form, demonstrating the potential of chemoenzymatic synthesis for medicinal chemistry and drug discovery.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Organic

Borane-Catalyzed Carbazolation Reactions of Aryldiazoacetates

Feifei He et al.

Summary: In this study, the tris(pentafluorophenyl)borane-catalyzed reaction of carbazole heterocycles with aryldiazoacetates was reported. It was demonstrated that selective N-H or C-H functionalization could be achieved with good yields under different substrate conditions. The method showed promising application potential in 41 examples.

ORGANIC LETTERS (2021)

Review Chemistry, Physical

Silver carbenoids derived from diazo compounds: A historical perspective on challenges and opportunities

Xiaolong Zhang et al.

Summary: This review article discusses the importance of transition-metal-catalyzed carbene transfer reactions in organic synthesis, with a focus on the advantages and specificities of silver catalysts over other transition metals. The specific reactions catalyzed by Ag(I) salts or complexes and their applications in total synthesis are highlighted, along with the detailed mechanisms and remaining challenges for the design of new silver catalysts.

CHEM CATALYSIS (2021)

Article Chemistry, Multidisciplinary

B(C6F5)3-Catalyzed site-selective N1-alkylation of benzotriazoles with diazoalkanes

Yunbo Zhao et al.

Summary: The study demonstrates a metal-free catalytic selective N-1 alkylation of benzotriazoles with diazoalkanes using 10 mol% of B(C6F5)(3), providing N-1-alkylated benzotriazoles in good to excellent yields. The protocol is successfully applied to gram-scale syntheses and a derivative with antimicrobial activity, showcasing its versatility and potential for practical applications.

CHEMICAL COMMUNICATIONS (2021)

Article Chemistry, Organic

B(C6F5)3-catalyzed O-H insertion reactions of diazoalkanes with phosphinic acids

Yangyang Zhang et al.

Summary: This study presents a highly efficient and environmentally friendly catalytic reaction for the synthesis of a variety of alpha-phosphoryloxy carbonyl compounds, with good to excellent yields. The protocol is characterized by operational simplicity, high atom economy, practicality, scalability, and environmental friendliness.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Borane catalysed cyclopropenation of arylacetylenes

Katarina Stefkova et al.

Summary: Triarylboranes have garnered significant attention as catalysts for C-C bond forming reactions due to their remarkable catalytic activities. In this study, the B(C6F5)(3) catalyzed cyclopropenation of arylacetylenes using donor-acceptor diazoesters has been successfully developed, resulting in the synthesis of a wide variety of functionalized cyclopropenes in good to excellent yields.

CHEMICAL COMMUNICATIONS (2021)

Article Chemistry, Multidisciplinary

Electrocatalytic C-N Coupling via Anodically Generated Hypervalent Iodine Intermediates

Asim Maity et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Triarylborane-Catalyzed Alkenylation Reactions of Aryl Esters with Diazo Compounds

Ayan Dasgupta et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Physical

Tris(pentafluorophenyl)borane-Catalyzed Cyclopropanation of Styrenes with Aryldiazoacetates

Joseph P. Mancinelli et al.

ACS CATALYSIS (2020)

Review Chemistry, Multidisciplinary

Halogenated triarylboranes: synthesis, properties and applications in catalysis

Jamie L. Carden et al.

CHEMICAL SOCIETY REVIEWS (2020)

Review Chemistry, Multidisciplinary

Recent progress on donor and donor-donor carbenes

Dong Zhu et al.

CHEMICAL SOCIETY REVIEWS (2020)

Article Chemistry, Inorganic & Nuclear

Addition reactions and diazomethane capture by the intramolecular P-O-B FLP: tBu2POBcat

Diya Zhu et al.

DALTON TRANSACTIONS (2020)

Article Chemistry, Multidisciplinary

Metal-Free Tandem Rearrangement/Lactonization: Access to 3,3-Disubstituted Benzofuran-2-(3H)-ones

Micol Santi et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Organic

Boron-Catalyzed Azide Insertion of α-Aryl α-Diazoesters

Htet Htet San et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Multidisciplinary Sciences

The reductive coupling of dinitrogen

Marc-Andre Legare et al.

SCIENCE (2019)

Article Chemistry, Organic

Boron-Catalyzed Carbonate Functionality Transfer Reaction

Santhosh Rao et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Chemistry, Multidisciplinary

Practical and regioselective amination of arenes using alkyl amines

Alessandro Ruffoni et al.

NATURE CHEMISTRY (2019)

Article Chemistry, Physical

Triarylborane-Catalyzed Reductive N-Alkylation of Amines: A Perspective

Yoichi Hoshimoto et al.

ACS CATALYSIS (2019)

Review Chemistry, Multidisciplinary

Dirhodium tetracarboxylates as catalysts for selective intermolecular C-H functionalization

Huw M. L. Davies et al.

NATURE REVIEWS CHEMISTRY (2019)

Review Chemistry, Multidisciplinary

Reductive Amination in the Synthesis of Pharmaceuticals

Oleg Afanasyev et al.

CHEMICAL REVIEWS (2019)

Article Chemistry, Applied

Boron-Catalyzed C-C Functionalization of Allyl Alcohols

Santhosh Rao et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

Review Chemistry, Organic

Recent developments in photochemical reactions of diazo compounds

Lukasz W. Ciszewski et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2019)

Article Chemistry, Organic

Boron-Catalyzed O-H Bond Insertion of α-Aryl α-Diazoesters in Water

Htet Htet San et al.

ORGANIC LETTERS (2018)

Article Chemistry, Multidisciplinary

1,1-Hydroboration and a Borane Adduct of Diphenyldiazomethane: A Potential Prelude to FLP-N2 Chemistry

Connie Tang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

Transition-Metal-Catalyzed Cross-Couplings through Carbene Migratory Insertion

Ying Xia et al.

CHEMICAL REVIEWS (2017)

Article Chemistry, Multidisciplinary

(C6F5)3B Catalyzed Chemoselective and ortho-Selective Substitution of Phenols with α-Aryl α-Diazoesters

Zhunzhun Yu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Organic

Enantioselective carbenoid insertion into C(sp3)-H bonds

J. V. Santiago et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2016)

Article Chemistry, Multidisciplinary

Stability and reactivity control of carbenoids: recent advances and perspectives

Viktoria H. Gessner

CHEMICAL COMMUNICATIONS (2016)

Article Chemistry, Multidisciplinary

Gold(I)-Catalyzed Diazo Cross-Coupling: A Selective and Ligand-Controlled Denitrogenation/Cyclization Cascade

Guangyang Xu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Review Chemistry, Multidisciplinary

Catalytic X-H insertion reactions based on carbenoids

Dennis Gillingham et al.

CHEMICAL SOCIETY REVIEWS (2013)

Article Chemistry, Inorganic & Nuclear

Bulky derivatives of boranes, boronic acids and boronate esters via reaction with diazomethanes

Rebecca C. Neu et al.

DALTON TRANSACTIONS (2013)

Article Chemistry, Inorganic & Nuclear

Insertion Reactions of Diazomethanes and Electrophilic Boranes

Rebecca C. Neu et al.

ORGANOMETALLICS (2012)

Review Multidisciplinary Sciences

Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion

Huw M. L. Davies et al.

NATURE (2008)

Review Chemistry, Multidisciplinary

Synthesis and properties of cyclopropane-derived peptidomimetics

Andreas Reichelt et al.

ACCOUNTS OF CHEMICAL RESEARCH (2006)