4.8 Article

Deoxygenative Haloboration and Enantioselective Chloroboration of Carbonyls

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

Multicomponent synthesis of a-chloro alkylboronic esters via visible-light-mediated dual catalysis

Bo Li et al.

Summary: a-Chloro alkylboronic (a-CAB) esters are bifunctional molecules that can exhibit distinct reactivity through the differences between carbon-chlorine and carbon-boron bonds. We developed a new visible-light-mediated dual catalytic process for the coupling of diaryliodonium salts, alkenes, and metal chlorides, which offers a broad scope of reactions and synthetic diversification. This transformation will be of great interest to synthetic and medicinal chemists in both academic and industrial settings.
Article Multidisciplinary Sciences

Electrochemically driven cross-electrophile coupling of alkyl halides

Wen Zhang et al.

Summary: Recent research in medicinal chemistry has found a correlation between an increase in sp(3) carbons in drug candidates and their improved success rate in clinical trials. This study focuses on the development of robust and selective methods for constructing carbon(sp(3))-carbon(sp(3)) bonds. By using electrochemistry, the researchers achieve the selective activation of alkyl halides based on their electronic and steric properties, allowing for high selectivity in carbon(sp(3))-carbon(sp(3)) cross-electrophile coupling. This new protocol shows improved chemoselectivity and does not require a transition metal catalyst.

NATURE (2022)

Article Chemistry, Organic

Ni-Catalyzed Radical-Promoted Defluoroalkylborylation of Trifluoromethyl Alkenes To Access gem-Difluorohomoallylic Boronates

Jian Qiu et al.

Summary: In this study, an efficient protocol for the construction of gem-difluorohomoallylic boronates was developed through a nickel-catalyzed radical promoted defluoroalkylborylation reaction under mild conditions, using α-trifluoromethyl alkenes and α-haloboronates as substrates. This reaction demonstrated a broad substrate scope, good functional group tolerance, and diverse transformations.

ORGANIC LETTERS (2022)

Article Chemistry, Physical

Deoxygenative Arylboration of Aldehydes via Copper and Nickel/ Photoredox Catalysis

Purui Zheng et al.

Summary: In this study, we developed a strategy for the deoxygenative arylboration of aldehydes using a dual nickel/photoredox catalysis regime and a radical intermediate. This method showed good compatibility with a wide variety of substrates and mild reaction conditions.

ACS CATALYSIS (2022)

Article Chemistry, Multidisciplinary

Modular and Fast Synthesis of Versatile Secondary α,α-Dialkyl Boronates via Deoxygenative Alkylboration of Aldehydes

Wenhao Xu et al.

Summary: Secondary alpha,alpha-dialkyl boronates are highly versatile compounds that are widely used. In this study, we report an unprecedented method for the deoxygenative alkylboration of aldehydes, providing a facile approach to access this type of products. This difunctionalization of aldehydes, instead of conventional alkenes, opens up new possibilities in the field.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Multidisciplinary

Photochemical Radical C-H Halogenation of Benzyl N-Methyliminodiacetyl (MIDA) Boronates: Synthesis of α-Functionalized Alkyl Boronates

Ling Yang et al.

Summary: A new method was proposed utilizing benzyl N-methyliminodiacetyl (MIDA) boronates for photochemical radical C-H halogenation, enabling successful fluorination, chlorination, and bromination reactions. The resulting brominated product could be further transformed into a variety of organic compounds, including those difficult to form with alpha-halo sp(2)-B boronate esters, by reaction with different nucleophiles. An activation effect of the B(MIDA) moiety was discovered.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

sp3 Bis-Organometallic Reagents via Catalytic 1,1-Difunctionalization of Unactivated Olefins

Shang-Zheng Sun et al.

Summary: A catalytic 1,1-difunctionalization of unactivated olefins is described for the synthesis of sp(3) bis-organometallic B,B(Si)-reagents. The protocol features exceptional reaction rates, mild conditions, wide scope, and exquisite selectivity pattern, providing a new platform for accessing sp(3) bis-organometallics.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Organic

Application of Allylzinc Reagents as Nucleophiles in Matteson Homologations

Oliver Andler et al.

Summary: Allylzinc reagents are versatile nucleophiles that exhibit excellent E selectivities in Matteson homologations. The resulting allylated boronic esters can be further converted into trifluoroborates or subjected to additional homologations, providing a useful tool for organic synthesis.

ORGANIC LETTERS (2021)

Article Multidisciplinary Sciences

Enantioselective catalytic 1,2-boronate rearrangements

Hayden A. Sharma et al.

Summary: This study presents a strategy for constructing a wide variety of trisubstituted stereocenters through enantioselective, catalytic 1,2-boronate rearrangements. The chiral building blocks produced in these reactions can undergo two sequential stereospecific elaborations to generate a wide assortment of trisubstituted stereocenters. The enantioselective reaction is catalyzed by a lithium-isothiourea-boronate complex, which promotes rearrangement through a dual-lithium-induced chloride abstraction orchestrated by Lewis basic functionality on the catalyst scaffold.

SCIENCE (2021)

Article Multidisciplinary Sciences

Dual Ni/photoredox-catalyzed asymmetric cross-coupling to access chiral benzylic boronic esters

Purui Zheng et al.

Summary: The authors reported a mild Ni/photoredox-catalyzed reductive cross-coupling of aryl iodides and alpha -chloroboranes, enriching the metallaphotoredox chemistry. This method enables the access to versatile benzylic boronic esters with good functional group tolerance and excellent enantioselectivities under mild conditions.

NATURE COMMUNICATIONS (2021)

Article Chemistry, Multidisciplinary

Catalytic Reductive Cross-Coupling between Aromatic Aldehydes and Arylnitriles

Atsuhisa Mitsui et al.

Summary: This study presents a novel approach for the chemoselective synthesis of alpha-hydroxy ketones through a reductive cross-coupling reaction between aromatic aldehydes and arylnitriles using a copper catalyst and a silylboronate as a reductant.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Article Chemistry, Organic

Ni-Catalyzed Reductive Allylation of α-Chloroboronates to Access Homoallylic Boronates

Yixian Lou et al.

Summary: The study presents a Ni-catalyzed reductive allylation of alpha-chloroboronates to efficiently produce homoallylic boronates, which can be easily converted into valuable homoallylic alcohols, amines, or 1,4-diboronates. This reaction demonstrates a broad substrate scope and good functional group compatibility, offering advantages over existing methods for the preparation of homoallylic boronates.

ORGANIC LETTERS (2021)

Article Chemistry, Multidisciplinary

A General Approach to Deboronative Radical Chain Reactions with Pinacol Alkylboronic Esters

Emy Andre-Joyaux et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Multidisciplinary Sciences

Chemodivergent transformations of amides using gem-diborylalkanes as pro-nucleophiles

Wei Sun et al.

NATURE COMMUNICATIONS (2020)

Article Chemistry, Multidisciplinary

Halohydroxylation of alkenyl MIDA boronates: switchable stereoselectivity induced by B(MIDA) substituent

Yao-Fu Zeng et al.

CHEMICAL COMMUNICATIONS (2020)

Article Chemistry, Multidisciplinary

Asymmetric Catalysis Using Aromatic Aldehydes as Chiral α-Alkoxyalkyl Anions

Kenya Yabushita et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Dual Functionalization of -Monoboryl Carbanions through Deoxygenative Enolization with Carboxylic Acids

Wei Sun et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Umpolung Arylation of Ambiphilic -Bromoalkyl Boronic Esters

Shang-Zheng Sun et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

A Coupling Approach for the Generation of α,α-Bis(enolate) Equivalents: Regioselective Synthesis of gem-Difunctionalized Ketones

Carmelo E. Iacono et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Review Chemistry, Organic

gem-Diborylalkanes: recent advances in their preparation, transformation and application

Rajender Nallagonda et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

Article Chemistry, Organic

Halogenation through Deoxygenation of Alcohols and Aldehydes

Jia Chen et al.

ORGANIC LETTERS (2018)

Article Chemistry, Organic

Geminal bis(boron) compounds: Their preparation and synthetic applications

Chaoqiang Wu et al.

TETRAHEDRON LETTERS (2018)

Article Chemistry, Multidisciplinary

Cobalt-Catalyzed Reductive Dimethylcyclopropanation of 1,3-Dienes

Jacob Werth et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Site-Selective Ni-Catalyzed Reductive Coupling of alpha-Haloboranes with Unactivated Olefins

Shang-Zheng Sun et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Multidisciplinary

Difunctionalization of ketones via gem-bis(boronates) to synthesize quaternary carbon with high selectivity

Purui Zheng et al.

CHEMICAL COMMUNICATIONS (2018)

Article Chemistry, Multidisciplinary

C-O Functionalization of α-Oxyboronates: A Deoxygenative gem-Diborylation and gem-Silylborylation of Aldehydes and Ketones

Lu Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Multidisciplinary

Synthesis of Branched Alkylboronates by Copper-Catalyzed Allylic Substitution Reactions of Allylic Chlorides with 1,1-Diborylalkanes

Junghoon Kim et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Transition-Metal-Free Regioselective Alkylation of Pyridine N-Oxides Using 1,1-Diborylalkanes as Alkylating Reagents

Woohyun Jo et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Reductive Cyclopropanations Catalyzed by Dinuclear Nickel Complexes

You-Yun Zhou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Oxidative Difunctionalization of Alkenyl MIDA Boronates: A Versatile Platform for Halogenated and Trifluoromethylated α-Boryl Ketones

Wen-Xin Lv et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Palladium(0)-Catalyzed Cross-Coupling of 1,1-Diboronates with Vinyl Bromides and 1,1-Dibromoalkenes

Huan Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

Nonracemic Allylic Boronates through Enantiotopic-Group-Selective Cross-Coupling of Geminal Bis(boronates) and Vinyl Halides

Bowman Potter et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Multidisciplinary

A Catalytic Enantiotopic-Group-Selective Suzuki Reaction for the Construction of Chiral Organoboronates

Chunrui Sun et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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)

Article Chemistry, Multidisciplinary

Boron-Containing Enamine and Enamide Linchpins in the Synthesis of Nitrogen Heterocycles

Jeffrey D. St Denis et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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, Multidisciplinary

Iridium-Catalyzed Chemoselective and Enantioselective Hydrogenation of (1-Chloro-1-Alkenyl) Boronic Esters

Ivana Gazic Smilovic et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Article Chemistry, Multidisciplinary

Chemoselective and Regiospecific Suzuki Coupling on a Multisubstituted sp3-Carbon in 1,1-Diborylalkanes at Room Temperature

Kohei Endo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Article Chemistry, Multidisciplinary

Catalytic diboration of aldehydes via insertion into the copper-boron bond

David S. Laitar et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Article Chemistry, Inorganic & Nuclear

Bromination of tri(isopropyl)boroxine and asymmetric synthesis of (2-cyano-3,3-dimethylcyclopropyl)boronic esters

DS Matteson et al.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2003)