4.8 Article

Ligand-Enabled Copper-Catalyzed Regio- and Stereoselective Allylboration of 1-Trifluoromethylalkenes

Related references

Note: Only part of the references are listed.
Review Chemistry, Organic

Catalytic Asymmetric Construction of CF3-Substituted Chiral sp3 Carbon Centers

Koji Hirano

Summary: This review focuses on the importance of organofluorine compounds in pharmaceuticals and agrochemicals, with particular emphasis on the challenges and recent advances in the catalytic enantioselective synthesis of sp(3) carbon-based alkyl-CF3-containing molecules.

SYNTHESIS-STUTTGART (2022)

Article Chemistry, Physical

Nickel-Catalyzed anti-Markovnikov Hydroalkylation of Trifluoromethylalkenes

Chuan Zhu et al.

Summary: Transition-metal-catalyzed difunctionalization of olefins is a powerful method to access complex molecules from bulk chemicals. In this study, a hydroalkylation reaction of trifluoromethylalkenes with alkyl halides under nickel catalysis was developed, leading to the efficient construction of 1,1,1-trifluoropropane derivatives. The commonly observed beta-fluoride elimination pathway was suppressed by using a competent proton donor, enabling the use of substrates featuring fluoroalkyl substituents.

ACS CATALYSIS (2022)

Review Chemistry, Multidisciplinary

Catalytic Enantioselective Allylic C F Bond Functionalization

Minyan Wang et al.

Summary: Catalytic enantioselective defluorinative functionalization of easily accessible allylic fluorines is considered as one of the most attractive strategies for creating allylic stereogenic centers with high enantioselectivity. Recent developments in this area have mainly focused on enantioselective defluoroarylation, enantioselective defluoroalkylation, enantioselective defluoroborylation, and other aspects. Despite the attention on mechanisms and limitations, it is hoped that this review provides a comprehensive overview to evaluate the prospects of this rapidly emerging field.

CHEMISTRY LETTERS (2021)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Highly Selective Protoboration of CF3-Containing 1,3-Dienes

Juanjuan Wu et al.

Summary: The study presents a copper-catalyzed highly selective protoboration reaction that can suppress defluorination and provide CF3-containing borated reagents. Functional group tolerance of this reaction is well demonstrated, with the products serving as versatile precursors for various transformations. By using a chiral diphosphine ligand, allylic boron reagents with a CF3-containing chiral center were synthesized for the first time. Additionally, in-depth DFT calculations were conducted to understand the mechanism behind the inhibition of defluorination.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Physical

Copper-Catalyzed Regio- and Enantioselective Hydroallylation of 1-Trifluoromethylalkenes: Effect of Crown Ether

Yuki Kojima et al.

Summary: This Cu-catalyzed reaction successfully constructs a C-sp3 chiral center with nonbenzylic and nonallylic CF3 substitution. The key to success lies in the use of an appropriate chiral bisphosphine ligand and 18-crown-6.

ACS CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Iridium-catalyzed enantioselective addition of an N-methyl C-H bond to α-trifluoromethylstyrenes via C-H activation

Daisuke Yamauchi et al.

Summary: The Ir-catalyzed enantioselective addition of an N-methyl C-H bond of 2-(methylamino)pyridine derivatives to alpha-trifluoromethylstyrenes proceeded via C-H activation to give chiral gamma-branched amine derivatives having a trifluoromethyl-substituted stereocenter. It was found that a bulky and electron-withdrawing group at the 3-position of 2-(methylamino)pyridines was necessary for the present C-H addition reaction catalyzed by a cationic iridium/chiral bisphosphine complex.

CHEMICAL COMMUNICATIONS (2021)

Article Chemistry, Multidisciplinary

Aminoazanium of DABCO: An Amination Reagent for Alkyl and Aryl Pinacol Boronates

Xingxing Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Chemistry, Multidisciplinary

Contribution of Organofluorine Compounds to Pharmaceuticals

Munenori Inoue et al.

ACS OMEGA (2020)

Review Chemistry, Physical

Strategies for the Catalytic Enantioselective Synthesis of α-Trifluoromethyl Amines

Chibueze Onyeagusi et al.

ACS CATALYSIS (2020)

Article Multidisciplinary Sciences

Current Contributions of Organofluorine Compounds to the Agrochemical Industry

Yuta Ogawa et al.

ISCIENCE (2020)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Enantioselective Allylboration of Alkynes: Synthesis of Highly Versatile Multifunctional Building Blocks

Eva Rivera-Chao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Catalytic Enantioselective Boryl and Silyl Substitution with Trifluoromethyl Alkenes: Scope, Utility, and Mechanistic Nuances of Cu-F β-Elimination

Paulo H. S. Paioti et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Biochemistry & Molecular Biology

DrugBank 5.0: a major update to the DrugBank database for 2018

David S. Wishart et al.

NUCLEIC ACIDS RESEARCH (2018)

Article Chemistry, Medicinal

Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design

Nicholas A. Meanwell

JOURNAL OF MEDICINAL CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

Ligand-Substrate Dispersion Facilitates the Copper-Catalyzed Hydroamination of Unactivated Olefins

Gang Lu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Inorganic & Nuclear

Elusive Phosphine Copper(l) Boryl Complexes: Synthesis, Structures, and Reactivity

Corinna Borner et al.

ORGANOMETALLICS (2017)

Review Chemistry, Multidisciplinary

London dispersion forces in sterically crowded inorganic and organometallic molecules

David J. Liptrot et al.

NATURE REVIEWS CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

Base-Controlled Completely Selective Linear or Branched Rhodium(I)-Catalyzed C-H ortho-Alkylation of Azines without Preactivation

Gael Tran et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

Carbon Trifluoromethylation Reactions of Hydrocarbon Derivatives and Heteroarenes

Concepcion Alonso et al.

CHEMICAL REVIEWS (2015)

Article Chemistry, Medicinal

Applications of Fluorine in Medicinal Chemistry

Eric P. Gillis et al.

JOURNAL OF MEDICINAL CHEMISTRY (2015)

Article Chemistry, Multidisciplinary

A Cu/Pd Cooperative Catalysis for Enantioselective Allylboration of Alkenes

Tao Jia et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Borylative Allyl-Allyl Coupling Reaction

Kazuhiko Semba et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

Enantiospecific sp2-sp3 coupling of secondary and tertiary boronic esters

Amadeu Bonet et al.

NATURE CHEMISTRY (2014)

Article Chemistry, Organic

Copper-Catalyzed Three-Component Carboboration of Alkynes and Alkenes

Hiroto Yoshida et al.

ORGANIC LETTERS (2013)

Article Chemistry, Multidisciplinary

Copper(I)-Catalyzed Formal Carboboration of Alkynes: Synthesis of Tri- and Tetrasubstituted Vinylboronates

Ricardo Alfaro et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Article Chemistry, Multidisciplinary

Enantioselective Construction of Quaternary Stereogenic Centers from Tertiary Boronic Esters: Methodology and Applications

Ravindra P. Sonawane et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Review Chemistry, Multidisciplinary

Understanding organofluorine chemistry. An introduction to the C-F bond

David O'Hagan

CHEMICAL SOCIETY REVIEWS (2008)

Review Multidisciplinary Sciences

Fluorine in pharmaceuticals:: Looking beyond intuition

Klaus Mueller et al.

SCIENCE (2007)

Review Chemistry, Inorganic & Nuclear

DFT studies of alkene insertions into Cu-B bonds in copper(I) boryl complexes

Li Dang et al.

ORGANOMETALLICS (2007)

Review Chemistry, Multidisciplinary

Fluorinated carbonyl and olefinic compounds: Basic character and asymmetric catalytic reactions

K Mikami et al.

CHEMICAL REVIEWS (2004)