☆ 4.8 Article

Sodium mediated deprotonative borylation of arenes using sterically demanding B(CH2SiMe3)3: unlocking polybasic behaviour and competing lateral borane sodiation

CHEMICAL SCIENCE (2023)

Related references

Note: Only part of the references are listed.

Article Chemistry, Multidisciplinary

Highly Reactive Hydrocarbon Soluble Alkylsodium Reagents for Benzylic Aroylation of Toluenes using Weinreb Amides

David E. Anderson et al.

Summary: Deaggregation of alkyl sodium NaCH2SiMe3 with polydentate nitrogen ligands allows the preparation and characterization of new, hydrocarbon soluble chelated alkylsodium reagents. These systems, equipped with significantly enhanced metalating power, can promote controlled sodiation of weakly acidic benzylic C-H bonds from a series of toluene derivatives under mild stoichiometric conditions. The successful isolation and determination of the structures of key organometallic intermediates provide useful mechanistic insights into these new sodium-mediated transformations.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Add to Collection

Article Chemistry, Multidisciplinary

Enhancing Metalating Efficiency of the Sodium Amide NaTMP in Arene Borylation Applications

Leonie J. Bole et al.

Summary: By mixing NaTMP with PMDETA, we have provided structural and mechanistic insights into the sodiation of non-activated arenes. The addition of B(OiPr)(3) not only intercepts the C-Ar-Na bond, but also drives the reaction towards the formation of more stable sodium aryl boronates.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Perdeuteration of Arenes via Hydrogen Isotope Exchange Catalyzed by the Superbasic Sodium Amide Donor Species NaTMPmiddotPMDETA

Andreu Tortajada et al.

Summary: In this study, the combination of a simple sodium amide and a tridentate Lewis donor was shown to catalytically promote hydrogen isotope exchange of nonactivated arenes under mild reaction conditions. The ability to partially metalate C6D6 and generate specific intermediates was demonstrated as the key to catalytic deuteration.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Add to Collection

Review Chemistry, Applied

Borata-Alkene Species as Nucleophilic Reservoir

Ricardo J. Maza et al.

Summary: The stability of alpha-Monoboryl anions and their resonance form borata-alkene systems are discussed in this review, along with the synthetic approaches and properties of the C=B bond. The characterization by X-ray diffraction and NMR data provide evidence for the partial boron-carbon double bond character, while reactivity studies demonstrate the nucleophilic potential of the C=B bond in electrophilic trapping examples. Homologation protocols with diborylmethane offer a facile method for introducing C(sp(3))-B bonds for subsequent transformations into functionalized products.

ADVANCED SYNTHESIS & CATALYSIS (2021)

Add to Collection

Article Chemistry, Organic

Controlling the Lewis Acidity and Polymerizing Effectively Prevent Frustrated Lewis Pairs from Deactivation in the Hydrogenation of Terminal Alkynes

Qiang Liu et al.

Summary: Two strategies were reported to prevent the deactivation of Frustrated Lewis pairs (FLPs) in the hydrogenation of terminal alkynes: reducing the Lewis acidity and polymerizing the Lewis acid. A polymeric Lewis acid (P-BPh3) with high stability was designed and synthesized, leading to excellent conversion and selectivity in the hydrogenation of terminal alkynes. This catalytic system works well for different substrates, and the P-BPh3 can be easily recycled.

ORGANIC LETTERS (2021)

Add to Collection

Article Chemistry, Multidisciplinary

A Boratafulvene

Tobias Heitkemper et al.

Summary: This study introduced structurally authenticated free B-alkyl boroles and evaluated the electronic implications of alkyl substitution. The research demonstrated that boratafulvenes can serve as nucleophilic synthons for boroles, providing a new avenue for synthetic strategies towards this highly reactive class of heterocycles. Boratafulvene was shown to react as a methylene transfer reagent in a bora-Wittig-type reaction, generating a borole oxide.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Bond Memory in Dynamically Determined Stereoselectivity

Vladislav A. Roytman et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Add to Collection

Article Chemistry, Multidisciplinary

Radical Reactions of Boron-Ate Complexes Promoting a 1,2-Metallate Rearrangement

Nicholas D. C. Tappin et al.

CHIMIA (2020)

Add to Collection

Review Chemistry, Applied

A Review on the Latest Progress of Chan-Lam Coupling Reaction

Jin-Quan Chen et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

Add to Collection

Article Chemistry, Organic

Alkali Metal Effects in Trans-Metal-Trapping (TMT): Comparing LiTMP with NaTMP in Cooperative MTMP/Ga(CH2SiMe3)3 Meta-lation Reactions

Ross McLellan et al.

SYNTHESIS-STUTTGART (2019)

Add to Collection

Article Chemistry, Physical

Organosodium compounds for catalytic cross-coupling

Sobi Asako et al.

NATURE CATALYSIS (2019)

Add to Collection

Review Chemistry, Multidisciplinary

Trans-Metal-Trapping: Concealed Crossover Complexes En Route to Transmetallation?

Marina Uzelac et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

Add to Collection

Article Chemistry, Physical

Chan-Evans-Lam Couplings with Copper Iminoarylsulfonate Complexes: Scope and Mechanism

Valerie Hardouin Duparc et al.

ACS CATALYSIS (2018)

Add to Collection

Review Chemistry, Applied

Recent Progress in the Radical Chemistry of Alkylborates and Alkylboronates

Ke Duan et al.

ADVANCED SYNTHESIS & CATALYSIS (2018)

Add to Collection

Article Chemistry, Inorganic & Nuclear

Trans-Metal-Trapping Meets Frustrated-Lewis-Pair Chemistry: Ga(CH2SiMe3)3-Induced C-H Functionalizations

Marina Uzelac et al.

INORGANIC CHEMISTRY (2017)

Add to Collection

Article Chemistry, Organic

Borata-Wittig olefination reactions of ketones, carboxylic esters and amides with bis(pentafluorophenyl)borata-alkene reagents

Tongdao Wang et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2017)

Add to Collection

Article Chemistry, Multidisciplinary

LiTMP Trans-Metal-Trapping of Fluorinated Aromatic Molecules: A Comparative Study of Aluminum and Gallium Carbanion Traps

Ross McLellan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Add to Collection

Article Chemistry, Multidisciplinary

Transforming LiTMP Lithiation of Challenging Diazines through Gallium Alkyl Trans-Metal-Trapping

Marina Uzelac et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Add to Collection

Article Chemistry, Multidisciplinary

Understanding the Subtleties of Frustrated Lewis Pair Activation of Carbonyl Compounds by N-Heterocyclic Carbene/Alkyl Gallium Pairings

Marina Uzelac et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

Add to Collection

Article Chemistry, Inorganic & Nuclear

Stabilized borata-alkene formation: structural features, reactions and the role of the counter cation

Sonja Kohrt et al.

DALTON TRANSACTIONS (2015)

Add to Collection

Review Chemistry, Multidisciplinary

Boron chemistry in a new light

Guillaume Duret et al.

CHEMICAL SCIENCE (2015)

Add to Collection

Review Chemistry, Multidisciplinary

Lithiation-Borylation Methodology and Its Application in Synthesis

Daniele Leonori et al.

ACCOUNTS OF CHEMICAL RESEARCH (2014)

Add to Collection

Review Chemistry, Multidisciplinary

Selection of boron reagents for Suzuki-Miyaura coupling

Alastair J. J. Lennox et al.

CHEMICAL SOCIETY REVIEWS (2014)

Add to Collection

Article Chemistry, Organic

Nickel-Catalyzed Multicomponent Coupling of Alkyne, Buta-1,3-diene, and Dimethylzinc under Carbon Dioxide

Yasuyuki Mori et al.

SYNTHESIS-STUTTGART (2014)

Add to Collection

Article Chemistry, Multidisciplinary

TMP (2,2,6,6-tetramethylpiperidide)-aluminate bases: lithium-mediated alumination or lithiation-alkylaluminium-trapping reagents?

David R. Armstrong et al.

CHEMICAL SCIENCE (2014)

Add to Collection

Article Chemistry, Inorganic & Nuclear

A Unique Frustrated Lewis Pair Pathway to Remarkably Stable Borata-Alkene Systems

Jiangang Yu et al.

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY (2013)

Add to Collection

Article Chemistry, Organic

A General Method for Suzuki-Miyaura Coupling Reactions Using Lithium Triisopropyl Borates

Matthias A. Oberli et al.

ORGANIC LETTERS (2012)

Add to Collection

Article Chemistry, Inorganic & Nuclear

Synthesis and Structures of [(Trimethylsilyl)methyl]sodium and -potassium with Bi- and Tridentate N-Donor Ligands

William Clegg et al.

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY (2011)

Add to Collection

Article Chemistry, Organic

Hydride as a Leaving Group in the Reaction of Pinacolborane with Halides under Ambient Grignard and Barbier Conditions. One-Pot Synthesis of Alkyl, Aryl, Heteroaryl, Vinyl, and Allyl Pinacolboronic Esters

Jacob W. Clary et al.

JOURNAL OF ORGANIC CHEMISTRY (2011)

Add to Collection

Article Chemistry, Organic

Highly Efficient One-Pot Access to Functionalized Arylboronic Acids via Noncryogenic Bromine/Magnesium Exchanges

Timo Leermann et al.

ORGANIC LETTERS (2011)

Add to Collection

Article Chemistry, Multidisciplinary

Highly Selective Metalations of Pyridines and Related Heterocycles Using New Frustrated Lewis Pairs or tmp-Zinc and tmp-Magnesium Bases with BF3 center dot OEt2

Milica Jaric et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

Add to Collection

Article Chemistry, Multidisciplinary

An Opportunity for Mg-Catalyzed Grignard-Type Reactions: Direct Coupling of Benzylic Halides with Pinacolborane with 10 mol % of Magnesium

Christine Pintaric et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Add to Collection

Article Chemistry, Multidisciplinary

Direct C-H Metalation with Chromium(II) and Iron(II): Transition-Metal Host/Benzenediide Guest Magnetic Inverse-Crown Complexes

Pablo Albores et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

Add to Collection

Article Multidisciplinary Sciences

Synergic Sedation of Sensitive Anions: Alkali-Mediated Zincation of Cyclic Ethers and Ethene

Alan R. Kennedy et al.

SCIENCE (2009)

Add to Collection

Article Chemistry, Inorganic & Nuclear

Alkyl abstraction from a trialkylyttrium complex [YR3(thf)2] (R = CH2SiMe3) using a group-13 element lewis acid ER3 (E = B, Al, Ga, In) -: Structural characterisation of the ion pair [YR2(thf)4]+[GaR4]- and of ER3 (E = B, Al, Ga)

Mathias U. Kramer et al.

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY (2007)

Add to Collection

Article Chemistry, Multidisciplinary

Alkali-metal-mediated zincation of anisole: Synthesis and structures of three instructive ortho-zincated complexes

William Clegg et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Add to Collection

Review Chemistry, Multidisciplinary

Beyond thermodynamic acidity: A perspective on the complex-induced proximity effect (CIPE) in deprotonation reactions

MC Whisler et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2004)

Add to Collection

Article Chemistry, Inorganic & Nuclear

Reactivity of the dimesityl-1,8-naphthalenediylborate anion: isolation of the borataalkene isomer and synthesis of 1,8-diborylnaphthalenes

JD Hoefelmeyer et al.

DALTON TRANSACTIONS (2004)

Add to Collection

Article Chemistry, Organic

Synthesis of ortho substituted arylboronic esters by in situ trapping of unstable lithio intermediates

J Kristensen et al.

ORGANIC LETTERS (2001)

Add to Collection

Article Chemistry, Multidisciplinary

Are n-BuLi/TMEDA-mediated arene ortholithiations directed?: Substituent-dependent rates, substituent-independent mechanisms

ST Chadwick et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2000)

Add to Collection

© Peeref 2019-2024. All rights reserved.