Facile preparation of organosilanes from benzylboronates and gem-diborylalkanes mediated by KOtBu

Article Chemistry, Organic

Palladium-catalyzed C-Si bond formation via denitrative cross-coupling of nitroarenes with hexamethyldisilane

Jiaxin Yao et al.

Summary: This study developed a novel method for the synthesis of arylsilane via Pd-catalyzed cross-coupling of hexamethyldisilane with nitroarenes. The method exhibits high selectivity and utilizes readily accessible chemical feedstocks.

ORGANIC CHEMISTRY FRONTIERS (2023)

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Review Chemistry, Multidisciplinary

Ni-catalyzed C-S bond construction and cleavage

Su Huang et al.

Summary: Sulfur-containing compounds have wide-ranging applications and are of great importance. The development of methods for constructing and transforming these compounds is crucial, and nickel-catalyzed cross-coupling reactions are important strategies. Sulfur-containing compounds are playing increasingly important roles in this field.

CHEMICAL SOCIETY REVIEWS (2022)

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Review Chemistry, Multidisciplinary

Decarboxylative Halogenation of Organic Compounds

Andrii Varenikov et al.

Summary: Decarboxylative halogenation is a crucial method for synthesizing organic halides by converting carboxylic acids to the corresponding organic halides. This method involves the synthesis of organic iodides, bromides, chlorides, and fluorides, providing a wide range of methods and advantages.

CHEMICAL REVIEWS (2021)

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Review Chemistry, Multidisciplinary

Recent Development of Aryl Diazonium Chemistry for the Derivatization of Aromatic Compounds

Fanyang Mo et al.

Summary: Aryl diazonium salts are essential building blocks in organic synthesis, and recent research has focused on new transformations involving the generation of radical intermediates and transition metal-catalyzed reactions using these salts. These developments significantly expand the synthetic chemist's toolbox for building aromatic carbon-carbon and carbon-heteroatom bonds, providing powerful tools for synthesizing and modifying complex molecular structures.

CHEMICAL REVIEWS (2021)

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Article Chemistry, Multidisciplinary

Nickel-Catalyzed, Reductive C(sp3)-Si Cross-Coupling of α-Cyano Alkyl Electrophiles and Chlorosilanes

Liangliang Zhang et al.

Summary: A new nickel/zinc-catalyzed cross-electrophile coupling reaction has been reported, utilizing alkyl electrophiles activated by an alpha-cyano group and chlorosilanes. Elemental zinc serves as the stoichiometric reductant in this reductive coupling process, allowing for the formation of a C(sp(3))-Si bond starting from two electrophilic reactants. This method differs from previous approaches that rely on the combination of carbon nucleophiles and silicon electrophiles.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Regio-controllable Cobalt-Catalyzed Sequential Hydrosilylation/Hydroboration of Arylacetylenes

Zhaoyang Cheng et al.

Summary: This study presents a controllable cobalt-catalyzed sequential hydrosilylation/hydroboration reaction of arylacetylenes, achieving high regioselectivities for all possible regio-outcomes. Adjusting the ligands of cobalt catalysts combined with dual catalysis relay strategy is crucial for achieving regio-chemistry control, which may inspire further exploration in diversity-oriented synthesis involving multiple additions.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Regio- and Stereoselective 1,2-Carboboration of Ynamides with Aryldichloroboranes

Cai You et al.

Summary: The study introduces a catalyst-free 1,2-carboboration reaction of ynamides, which shows high yields with complete regio- and stereoselectivity, yielding valuable enamide compounds with synthetic potential.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Cobalt-Catalyzed One-Pot Asymmetric Difunctionalization of Alkynes to Access Chiral gem-(Borylsilyl)alkanes

Yang'en You et al.

Summary: A chiral-selective one-pot reaction has been developed to transform terminal alkynes into gem-(borylsilyl)alkanes using a specific cobalt catalyst, achieving high enantioselectivity.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Enantioselective Cobalt-Catalyzed Cascade Hydrosilylation and Hydroboration of Alkynes to Access Enantioenriched 1,1-Silylboryl Alkanes

Shengnan Jin et al.

Summary: Enantioenriched 1,1-silylboryl alkanes are valuable chiral multifunctional compounds, serving as important building blocks in asymmetric synthesis and medicinal chemistry. A cobalt-catalyzed hydrosilylation/hydroboration cascade has been developed for the efficient synthesis of these compounds, exhibiting impressive levels of selectivity and control in the hydrofunctionalization processes.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Multidisciplinary

Direct synthesis and applications of solid silylzinc reagents

Revathi Chandrasekaran et al.

Summary: The study demonstrates the successful direct synthesis of PhMe2SiZnI and Me3SiZnI reagents using TMEDA ligand, showing longer storage time and broader applicability. These reagents exhibit excellent performance in cross-coupling reactions, including alkylation, arylation, and allylation.

CHEMICAL SCIENCE (2021)

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Review Chemistry, Multidisciplinary

Recent advances in asymmetric borylation by transition metal catalysis

Jiefeng Hu et al.

Summary: Researchers have devoted much effort in exploring synthetic methodologies for the preparation of chiral organoboronates. Among the known methods, asymmetric catalysis has emerged as a practical and highly efficient strategy for their straightforward preparation, with recent remarkable advances in approaches such as asymmetric borylative addition, asymmetric allylic borylation, and stereospecific cross-coupling borylation employing transition-metal catalysis with a chiral ligand.

CHEMICAL SOCIETY REVIEWS (2021)

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Review Chemistry, Organic

Recent developments in decarboxylative C(aryl)-X bond formation from (hetero)aryl carboxylic acids

Ruchi Sharma et al.

Summary: Decarboxylative coupling reactions using readily available (hetero)aryl carboxylic acids are an efficient approach for forming new C-C and C-X bonds, with the advantage of eliminating CO2 as a by-product and being more environmentally friendly. This review summarizes recent developments in ipso-decarboxylative C-X bond formations using (hetero)aryl carboxylic acids, and highlights current limitations and future research opportunities in aryl-decarboxylative coupling reactions.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Stereospecific and Chemoselective Copper-Catalyzed Deaminative Silylation of Benzylic Ammonium Triflates

Jonas Scharfbier et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Multidisciplinary

Ketone Synthesis from Benzyldiboronates and Esters: Leveraging α-Boryl Carbanions for Carbon-Carbon Bond Formation

Boran Lee et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Review Chemistry, Multidisciplinary

Methodologies and Strategies for Selective Borylation of C-Het and C-C Bonds

Minyan Wang et al.

CHEMICAL REVIEWS (2020)

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Article Chemistry, Multidisciplinary

Cross-Electrophile C(sp2)-Si Coupling of Vinyl Chlorosilanes

Jicheng Duan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Multidisciplinary

Metal-Free Direct Deoxygenative Borylation of Aldehydes and Ketones

Jianbin Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Organic

Synthesis of Alkyl Silanes via Reaction of Unactivated Alkyl Chlorides and Triflates with Silyl Lithium Reagents

Shubhadip Mallick et al.

ORGANIC LETTERS (2020)

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Review Chemistry, Multidisciplinary

C-C and C-X coupling reactions of unactivated alkyl electrophiles using copper catalysis

Li-Jie Cheng et al.

CHEMICAL SOCIETY REVIEWS (2020)

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Article Chemistry, Physical

Conjugated Polymers Inspired by Crystalline Silicon

Eric A. Marro et al.

CHEMISTRY OF MATERIALS (2019)

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Article Chemistry, Multidisciplinary

Copper-Catalyzed Triboration: Straightforward, Atom-Economical Synthesis of 1,1,1-Triborylalkanes from Terminal Alkynes and HBpin

Xiaocui Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Physical

C(sp3)-Si Cross-Coupling

Susanne Baehr et al.

ACS CATALYSIS (2019)

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Article Chemistry, Multidisciplinary

Catalyst-controlled regiodivergent ring-opening C(sp3)-Si bond-forming reactions of 2-arylaziridines with silylborane enabled by synergistic palladium/copper dual catalysis

Youhei Takeda et al.

CHEMICAL SCIENCE (2019)

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Article Chemistry, Medicinal

Quest for Novel Chemical Entities through Incorporation of Silicon in Drug Scaffolds

Remya Ramesh et al.

JOURNAL OF MEDICINAL CHEMISTRY (2018)

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Article Chemistry, Physical

Enantioselective Synthesis of Nonracemic Geminal Silylboronates by Pt-Catalyzed Hydrosilylation

Adam A. Szymaniak et al.

ACS CATALYSIS (2018)

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Article Chemistry, Multidisciplinary

Bench-Stable Stock Solutions of Silicon Grignard Reagents: Application to Iron- and Cobalt-Catalyzed Radical C(sp3)-Si Cross-Coupling Reactions

Weichao Xue et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

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Review Chemistry, Multidisciplinary

Boron reagents for divergent radiochemistry

Thomas C. Wilson et al.

CHEMICAL SOCIETY REVIEWS (2018)

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Article Chemistry, Physical

Highly tunable multi-borylation of gem-difluoroalkenes via copper catalysis

Jiefeng Hu et al.

NATURE CATALYSIS (2018)

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Review Chemistry, Physical

Recent Advances in Transition-Metal-Catalyzed Synthetic Transformations of Organosilicon Reagents

Takeshi Komiyama et al.

ACS CATALYSIS (2017)

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Article Chemistry, Multidisciplinary

Palladium-Catalyzed Cross-Coupling of Silyl Electrophiles with Alkylzinc Halides: A Silyl-Negishi Reaction

Andrew P. Cinderella et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

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Article Chemistry, Multidisciplinary

Catalytic B-C Coupling by Si/B Exchange: A Versatile Route to π-Conjugated Organoborane Molecules, Oligomers, and Polymers

Artur Lik et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

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Article Multidisciplinary Sciences

Photoinduced decarboxylative borylation of carboxylic acids

Alexander Fawcett et al.

SCIENCE (2017)

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Article Chemistry, Physical

Palladium-Catalyzed Cross-Coupling of Monochlorosilanes and Grignard Reagents

Bojan Vulovic et al.

ACS CATALYSIS (2017)

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Article Chemistry, Multidisciplinary

Copper-Catalyzed Decarboxylative Radical Silylation of Redox-Active Aliphatic Carboxylic Acid Derivatives

Weichao Xue et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

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Review Chemistry, Multidisciplinary

Diboron(4) Compounds: From Structural Curiosity to Synthetic Workhorse

Emily C. Neeve et al.

CHEMICAL REVIEWS (2016)

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Review Chemistry, Multidisciplinary

Modern Transition-Metal-Catalyzed Carbon-Halogen Bond Formation

David A. Petrone et al.

CHEMICAL REVIEWS (2016)

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Review Chemistry, Inorganic & Nuclear

The chemistry of organo silanetriols

Rudolf Pietschnig et al.

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Article Chemistry, Multidisciplinary

Copper-Catalyzed Cross-Coupling of Silicon Pronucleophiles with Unactivated Alkyl Electrophiles Coupled with Radical Cyclization

Weichao Xue et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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Article Chemistry, Multidisciplinary

Silicon-Carbon Bond Formation via Nickel-Catalyzed Cross-Coupling of Silicon Nucleophiles with Unactivated Secondary and Tertiary Alkyl Electrophiles

Crystal K. Chu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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Review Chemistry, Multidisciplinary

Transition-Metal-Catalyzed Cleavage of C-N Single Bonds

Kunbing Ouyang et al.

CHEMICAL REVIEWS (2015)

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Review Chemistry, Multidisciplinary

Catalytic Silylation of Unactivated C-H Bonds

Chen Cheng et al.

CHEMICAL REVIEWS (2015)

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Review Chemistry, Multidisciplinary

Boron-selective reactions as powerful tools for modular synthesis of diverse complex molecules

Liang Xu et al.

CHEMICAL SOCIETY REVIEWS (2015)

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Review Chemistry, Applied

Why You Really Should Consider Using Palladium-Catalyzed Cross-Coupling of Silanols and Silanolates

Scott E. Denmark et al.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2015)

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Article Chemistry, Inorganic & Nuclear

Facile Arylation of Four-Coordinate Boron Halides by Borenium Cation Mediated Boro-desilylation and -destannylation

Daniel L. Crossley et al.

ORGANOMETALLICS (2015)

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Review Chemistry, Multidisciplinary

Stereospecific Couplings of Secondary and Tertiary Boronic Esters

Daniele Leonori et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

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Review Chemistry, Multidisciplinary

Selection of boron reagents for Suzuki-Miyaura coupling

Alastair J. J. Lennox et al.

CHEMICAL SOCIETY REVIEWS (2014)

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Article Chemistry, Multidisciplinary

Simple Access to Elusive α-Boryl Carbanions and Their Alkylation: An Umpolung Construction for Organic Synthesis

Kai Hong et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Article Multidisciplinary Sciences

Asymmetric synthesis from terminal alkenes by cascades of diboration and cross-coupling

Scott N. Mlynarski et al.

NATURE (2014)

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News Item Chemistry, Multidisciplinary

ASYMMETRIC SYNTHESIS Cascades of catalytic selectivity

Rian D. Dewhurst et al.

NATURE CHEMISTRY (2014)

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Article Chemistry, Medicinal

Organosilicon Molecules with Medicinal Applications

Annaliese K. Franz et al.

JOURNAL OF MEDICINAL CHEMISTRY (2013)

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Article Chemistry, Multidisciplinary

Silyl-substituted 1,3-butadienes for Diels-Alder reaction, ene reaction and allylation reaction

Fei Zhao et al.

CHEMICAL COMMUNICATIONS (2011)

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Review Chemistry, Multidisciplinary

Expanding the scope of transformations of organoboron species: carbon-carbon bond formation with retention of configuration

Cathleen M. Crudden et al.

CHEMICAL COMMUNICATIONS (2009)

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Article Chemistry, Organic

Perfluoroalkyl borates and boronic esters:: new promising partners for Suzuki and Petasis reactions

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TETRAHEDRON LETTERS (2003)

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Facile preparation of organosilanes from benzylboronates and gem-diborylalkanes mediated by KOtBu

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