Computational Assessment of the Mechanistic Journey in Chan-Lam-Based Arylation of Imidazoles.
Sign Up to like & getrecommendations! Published in 2024 at "Inorganic chemistry"
DOI: 10.1021/acs.inorgchem.4c00416
Abstract: Cu(II)-catalyzed C-N bond formation reactions remain one of most widely practiced and powerful protocols for the synthesis of value-added chemicals, bioactive molecules, and materials. Despite numerous experimental contributions, the overall mechanistic understanding of the C-N… read more here.
Keywords: chan lam; kcal mol; arylation imidazoles; computational assessment ... See more keywords
Synthesis of N-Vinyl Cinnamaldehyde Nitrones through Atropisomeric Quinoxaline-Derived N,N,O-Ligand-Promoted Chan-Lam Reaction.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c02288
Abstract: A type of quinoxaline-derived tridentate N,N,O-ligand was synthesized in good to excellent yields over three steps through iodination of 2-aryl indoles, sequential Kornblum-type oxidation with DMSO, and capture by 1,2-diaminobenzenes. The prepared atropisomeric N,N,O-ligand was… read more here.
Keywords: vinyl cinnamaldehyde; synthesis vinyl; chan lam; quinoxaline derived ... See more keywords
Data Science-Driven Discovery of Optimal Conditions and a Condition-Selection Model for the Chan-Lam Coupling of Primary Sulfonamides.
Sign Up to like & getrecommendations! Published in 2025 at "ACS catalysis"
DOI: 10.1021/acscatal.4c07972
Abstract: Secondary N-arylsulfonamides are common in pharmaceutical compounds owing to their valuable physicochemical properties. Direct N-arylation of primary sulfonamides presents a modular approach to this scaffold but remains a challenging disconnection for transition metal-catalyzed cross coupling… read more here.
Keywords: chan lam; primary sulfonamides; model; lam coupling ... See more keywords
Mechanistic Insight Enables Practical, Scalable, Room Temperature Chan–Lam N-Arylation of N-Aryl Sulfonamides
Sign Up to like & getrecommendations! Published in 2018 at "ACS Catalysis"
DOI: 10.1021/acscatal.8b03238
Abstract: Sulfonamides are profoundly important in pharmaceutical design. C–N cross-coupling of sulfonamides is an effective method for fragment coupling and structure–activity relationship (SAR) mining. However, cross-coupling of the important N-arylsulfonamide pharmacophore has been notably unsuccessful. Here,… read more here.
Keywords: mechanistic insight; room temperature; chan; lam arylation ... See more keywords
Biomolecule-Compatible Dehydrogenative Chan-Lam Coupling of Free Sulfilimines.
Sign Up to like & getrecommendations! Published in 2022 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.2c04627
Abstract: Inspired by the discovery of a S═N bond in the collagen IV network and its essential role in stabilizing basement membranes, sulfilimines have drawn much attention in the fields of chemistry and biology. However, their… read more here.
Keywords: chan lam; dehydrogenative chan; lam coupling; biomolecule compatible ... See more keywords
Enantioconvergent Chan-Lam Coupling: Synthesis of Chiral Benzylic Amides via Cu-Catalyzed Deborylative Amidation.
Sign Up to like & getrecommendations! Published in 2025 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.5c05884
Abstract: The Chan-Lam coupling represents one of the most effective methods for constructing C-N bonds due to its mild reaction conditions and broad functional group compatibility. However, asymmetric versions of this transformation to forge C(sp3)-N bonds… read more here.
Keywords: chan lam; coupling synthesis; chan; lam coupling ... See more keywords
Autocatalytic photoredox Chan-Lam coupling of free diaryl sulfoximines with arylboronic acids
Sign Up to like & getrecommendations! Published in 2021 at "Nature Communications"
DOI: 10.1038/s41467-021-21156-w
Abstract: N-Arylation of NH-sulfoximines represents an appealing approach to access N-aryl sulfoximines, but has not been successfully applied to NH-diaryl sulfoximines. Herein, a copper-catalyzed photoredox dehydrogenative Chan-Lam coupling of free diaryl sulfoximines and arylboronic acids is… read more here.
Keywords: coupling free; lam coupling; copper; chan ... See more keywords
Overcoming limitations in Chan-Lam amination with alkylboronic esters via aminyl radical substitution
Sign Up to like & getrecommendations! Published in 2025 at "Nature Communications"
DOI: 10.1038/s41467-025-64155-x
Abstract: Chan-Lam coupling represents one of the most reliable methods for constructing C(sp2)−N bonds under mild conditions. However, application of this technology as a general platform for C(sp3)−N bond assembly remains a longstanding challenge due to… read more here.
Keywords: chan lam; via aminyl; boron; lam coupling ... See more keywords
Oxidative cross-coupling processes inspired by the Chan-Lam reaction.
Sign Up to like & getrecommendations! Published in 2021 at "Chemical communications"
DOI: 10.1039/d1cc00213a
Abstract: The Cu-catalyzed oxidative cross-coupling of N- and O-nucleophiles with aryl boronic acids (the Chan-Lam reaction) remains among the most useful approaches to prepare aniline and phenol derivatives. The combination of high chemoselectivity, mild reaction conditions,… read more here.
Keywords: lam reaction; oxidative cross; reaction; cross coupling ... See more keywords
First atroposelective Chan-Lam coupling for the synthesis of C-N linked biaryls.
Sign Up to like & getrecommendations! Published in 2024 at "Chemical communications"
DOI: 10.1039/d3cc05447k
Abstract: The first atroposelective Chan-Lam coupling for the synthesis of C-N axial enantiomers is reported with good yields and ee. MnO2 additive is crucial for the success of the coupling. The longstanding problem of the lack… read more here.
Keywords: chan lam; coupling synthesis; atroposelective chan; synthesis ... See more keywords
Advances in Carbon–Element Bond Construction under Chan–Lam Cross-Coupling Conditions: A Second Decade
Sign Up to like & getrecommendations! Published in 2020 at "Synthesis"
DOI: 10.1055/s-0040-1705971
Abstract: Copper-mediated carbon–heteroatom bond-forming reactions involving a wide range of substrates have been in the spotlight for many organic chemists. This review highlights developments between 2010 and 2019 in both stoichiometric and catalytic copper-mediated reactions, and… read more here.
Keywords: bond; bond formation; copper; chan lam ... See more keywords