Direct benzylation of amines with benzylic alcohols catalyzed by palladium/phosphine-borane catalyst system

Abstract Direct catalytic benzylation of amines with benzylic alcohols to give benzylamines has been newly developed by using palladium/phosphine-borane catalyst system. In this catalytic reaction, the linking between both phosphine and borane moieties in the ligand is very important. Hydroxy group of benzylic alcohols is activated by Lewis acidic borane to form a benzylpalladium intermediate which is attacked by amines to give benzylamine products

• Publication year

  2020

• Venue

  Tetrahedron Letters

• Publication date

  2020-10-08

• Fields of study

  Chemistry

• Identifiers
  DOI 10.1016/j.tetlet.2020.152537
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar

• No claims are published for this paper.

• No concepts are published for this paper.

• Highly Diastereoselective Synthesis of Trifluoromethyl Indolines by Interceptive Benzylic Decarboxylative Cycloaddition of Nonvinyl, Trifluoromethyl Benzoxazinanones with Sulfur Ylides under Palladium Catalysis.

  2018cited by this paper
• Direct Allylic Amination of Allylic Alcohol Catalyzed by Palladium Complex Bearing Phosphine-Borane Ligand.

  2017cited by this paper
• Pd/C as an Efficient and Reusable Catalyst for the Selective N‐Alkylation of Amines with Alcohols

  2016cited by this paper
• Production of Csp3–Csp3 Bonds through Palladium-Catalyzed Tsuji–Trost-Type Reactions of (Hetero)Benzylic Substrates

  2016cited by this paper
• Complexes of ambiphilic ligands: reactivity and catalytic applications.

  2016cited by this paper
• Palladium-Catalyzed Asymmetric Benzylic Alkylation of Active Methylene Compounds with α-Naphthylbenzyl Carbonates and Pivalates.

  2016cited by this paper
• Palladium-Catalyzed Benzylic CH Benzylation via Bis-Benzylpalladium(II) Complexes in Water: An Effective Pathway for the Direct Construction of N-(1,2-Diphenylethyl)anilines

  2015cited by this paper
• Direct cross-coupling of benzyl alcohols to construct diarylmethanes via palladium catalysis.

  2015cited by this paper
• A general Pd-catalyzed α- and γ-benzylation of aldehydes for the formation of quaternary centers.

  2015cited by this paper
• Structure and reactivity of late transition metal η³-benzyl complexes.

  2014cited by this paper
• Mercaptobenzoic acid-palladium(0) complexes as active catalysts for S-benzylation with benzylic alcohols via (η(3)-benzyl)palladium(II) cations in water.

  2014cited by this paper
• Monobenzofused 1,4-azaborines: synthesis, characterization, and discovery of a unique coordination mode.

  2014cited by this paper
• Retro-Claisen benzylation: direct use of benzyl alcohols in Pd-catalyzed couplings with nitriles.

  2014cited by this paper
• An Efficient Palladium-Catalyzed N-Alkylation of Amines Using Primary and Secondary Alcohols

  2013cited by this paper
• ortho-(Dimesitylboryl)phenylphosphines: Positive Boryl Effect in the Palladium-Catalyzed Suzuki–Miyaura Coupling of 2-Chloropyridines

  2013cited by this paper
• N-Benzylation/Benzylic CH Amidation Cascade by the (η3-Benzyl)palladium System in Aqueous Media: An Effective Pathway for the Direct Construction of 3-Phenyl-3,4-dihydro- (2H)-1,2,4-benzothiadiazine 1,1-Dioxides

  2013cited by this paper
• Palladium-catalyzed asymmetric benzylation of azlactones.

  2013cited by this paper
• Pd-catalyzed C–H activation in water: synthesis of bis(indolyl)methanes from indoles and benzyl alcohols

  2013cited by this paper
• Mechanistic Studies for Synthesis of Bis(indolyl)methanes: Pd-Catalyzed C–H Activation of Indole–Carboxylic Acids with Benzyl Alcohols in Water

  2013cited by this paper
• Synthesis of arylacetates from benzylic alcohols and oxalate esters through decarboxylative coupling.

  2013cited by this paper
• Pd-catalyzed benzylic C-H amidation with benzyl alcohols in water: a strategy to construct quinazolinones.

  2012cited by this paper
• Benzylic phosphates as electrophiles in the palladium-catalyzed asymmetric benzylation of azlactones.

  2012cited by this paper
• Palladium-catalyzed C3-benzylation of indoles.

  2012cited by this paper
• Intramolecular SN'-type aromatic substitution of benzylic carbonates at their para-position.

  2012cited by this paper
• Palladium-catalyzed benzylation of unprotected anthranilic acids with benzyl alcohols in water.

  2011cited by this paper
• A new insight into ortho-(dimesitylboryl)diphenylphosphines: applications in Pd-catalyzed Suzuki-Miyaura couplings and evidence for secondary π-interaction.

  2011cited by this paper
• PdCl2-catalyzed efficient allylation and benzylation of heteroarenes under ligand, base/acid, and additive-free conditions.

  2011cited by this paper
• Enantiodivergence in alkylation of 1-(6-methoxynaphth-2-yl)ethyl acetate by potassium dimethyl malonate catalyzed by chiral palladium-DUPHOS complex

  2010cited by this paper
• Palladium-catalyzed asymmetric benzylation of 3-aryl oxindoles.

  2010cited by this paper
• Synthesis of 3,3-disubstituted oxindoles by palladium-catalyzed tandem reaction of 2-(alkynyl)aryl isocyanates with benzylic alcohols.

  2010cited by this paper
• A 1,1′-ferrocenyl phosphine-borane: synthesis, structure and evaluation in Rh-catalyzed hydroformylation

  2010cited by this paper
• Activation and functionalization of benzylic derivatives by palladium catalysts.

  2008cited by this paper
• pi-Acidic alkene ligand effects in Pd-catalysed cross-coupling processes: exploiting the interaction of dibenzylidene acetone (dba) and related ligands with Pd(0) and Pd(II).

  2008cited by this paper
• Use of acetate as a leaving group in palladium-catalyzed nucleophilic substitution of benzylic esters

  2007cited by this paper
• Palladium-catalyzed nucleophilic substitution of diarylmethyl carbonates with malonate carbanions

  2007cited by this paper
• Transformation of carbonates into sulfones at the benzylic position via palladium-catalyzed benzylic substitution.

  2005cited by this paper
• Asymmetric palladium-catalyzed benzylic nucleophilic substitution: high enantioselectivity with the DUPHOS family ligands

  2005cited by this paper
• Palladium-catalyzed benzylation of active methine compounds without additional base: remarkable effect of 1,5-cyclooctadiene.

  2004cited by this paper
• Palladium-catalyzed nucleophilic benzylic substitutions of benzylic esters.

  2003cited by this paper
• Asymmetric palladium-catalyzed nucleophilic substitution of 1-(2-naphthyl)ethyl acetate by dimethyl malonate anion

  2003cited by this paper
• Direct Carbonylation of Benzyl Alcohol and Its Analogs Catalyzed by Palladium and HI in Aqueous Systems and Mechanistic Studies.

  1998cited by this paper
• Catalytic conversions in water, part 8: carbonylation and hydrocarboxylation reactions catalyzed by palladium trisulfonated triphenylphosphine complexes

  1998cited by this paper
• Catalytic conversions in water. Part 5: Carbonylation of 1‐(4‐isobutylphenyl)ethanol to ibuprofen catalysed by water‐soluble palladium–phosphine complexes in a two‐phase system

  1997cited by this paper
• DMF as a dimethylamine equivalent in the palladium-catalyzed nucleophilic substitution of naphthylmethyl and allyl acetates

  1997cited by this paper
• Palladium-catalyzed substitution of esters of naphthylmethanols, 1-naphthylethanols, and analogues by sodium dimethyl malonate. Stereoselective synthesis from enantiomerically pure substrates

  1995cited by this paper
• Palladium-catalyzed nucleophilic substitution of napht hylmethyl and 1-naphthylethyl esters

  1992cited by this paper
• An investigation of the palladium-catalyzed, formate-mediated hydroxycarbonylation of optically active 1-arylethyl esters

  1991cited by this paper

• Extended Synthetic Pathways Towards Dialkyl-Substituted Phosphanylboranes

  2025cites this paper
• Gold‐Catalyzed Conia‐Ene Reaction of Malonate Derivatives Bearing An Alkyne Moiety by Using a Phosphine–Borane Ligand

  2025cites this paper
• Introduction of a Tropine-based Dicationic Catalyst for the N-Boc Protection and Acetylation of Amines under Solvent-free Conditions

  2024cites this paper
• Borrowing Hydrogen Amination Reactions: A Complex Analysis of Trends and Correlations of the Various Reaction Parameters

  2022cites this paper
• Direct Use of Benzylic Alcohols for Multicomponent Synthesis of 2‐Aryl Quinazolinones Utilizing the π‐Benzylpalladium(II) System in Water

  2021cites this paper