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   Articles with "sp3 arylation" as a keyword



C(sp3)-Arylation by Conformationally Accelerated Intramolecular Nucleophilic Aromatic Substitution (SNAr)

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recommendations! Published in 2022 at "Accounts of Chemical Research"

DOI: 10.1021/acs.accounts.2c00184

Abstract: Conspectus The asymmetric synthesis of heavily substituted benzylic stereogenic centers, prevalent in natural products, therapeutics, agrochemicals, and catalysts, is an ongoing challenge. In this Account, we outline our contribution to this endeavor, describing our discovery… read more here.

Keywords: substitution; aryl; conformationally accelerated; accelerated intramolecular ... See more keywords

Post-Assembly Modification of Peptides by Ligand-Enabled β-C(sp3)-H Arylation of Alanine at the C-Terminus: Overcoming the Inhibition Effect of Peptide Bonds.

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recommendations! Published in 2021 at "Organic letters"

DOI: 10.1021/acs.orglett.1c01481

Abstract: Postassembly modification of peptides via C(sp3)-H functionalization on aliphatic side chains provides a straightforward approach to access functionalized peptides as therapeutics. However, C(sp3)-H functionalization of C-terminal residues remains underdeveloped due to the inhibition effect of… read more here.

Keywords: inhibition effect; ligand enabled; modification peptides; alanine terminus ... See more keywords

Post-Assembly Modification of Head-to-Tail Cyclic Peptides by Methionine-Directed β-C(sp3)-H Arylation.

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recommendations! Published in 2022 at "Organic letters"

DOI: 10.1021/acs.orglett.2c02253

Abstract: Peptide modification by C(sp3)-H functionalization of internal residues remains a major challenge due to the inhibitory effect of peptide bonds. In this work, we developed a methionine-directed β-C(sp3)-H arylation method for internal alanine functionalization. By… read more here.

Keywords: methionine directed; directed sp3; head; head tail ... See more keywords

MPAI-Ligand Accelerated Pd-Catalyzed C(sp3)-H Arylation of Free Aliphatic Acids.

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recommendations! Published in 2022 at "Organic letters"

DOI: 10.1021/acs.orglett.2c02933

Abstract: Here, we report the development of a class of bifunctional monoprotected amino-imidazoline (MPAI) ligands and their applications in Pd-catalyzed C(sp3)-H arylation of free aliphatic acids. The newly developed MPAI ligand allows the use of 1.0… read more here.

Keywords: free aliphatic; mpai ligand; catalyzed sp3; aliphatic acids ... See more keywords

Studies towards the Enantioselective Synthesis of Cryptowolinol via Pd0-Catalyzed C(sp3)–H Arylation/Parallel Kinetic Resolution

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recommendations! Published in 2024 at "Organic Letters"

DOI: 10.1021/acs.orglett.4c00386

Abstract: We report a model study towards the enantioselective synthesis of the dibenzopyrrocoline alkaloid (−)-cryptowolinol. The key step involves a challenging enantioselective Pd0-catalyzed C(sp3)–H arylation performed with a chiral NHC ligand, which proceeds via parallel kinetic… read more here.

Keywords: enantioselective synthesis; catalyzed sp3; pd0 catalyzed; towards enantioselective ... See more keywords
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Pd/Cu-Catalyzed Cascade C(sp3)-H Arylation and Intramolecular C-N Coupling: A One-Pot Synthesis of 3,4-2 H-Quinolinone Skeletons.

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recommendations! Published in 2019 at "Organic letters"

DOI: 10.1021/acs.orglett.9b00214

Abstract: In this letter, we successfully explored a cascade Pd/Cu-catalyzed intermolecular C(sp3)-H arylation of amides and intramolecular C-N coupling reaction. This method provides a one-pot strategy to synthesize 3,4-2 H-quinolinone with good regioselectivity of C-H arylation… read more here.

Keywords: arylation; intramolecular coupling; sp3 arylation; one pot ... See more keywords

Ligand-Enabled, Palladium-Catalyzed β-C(sp3)-H Arylation of Weinreb Amides.

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recommendations! Published in 2018 at "ACS catalysis"

DOI: 10.1021/acscatal.8b03014

Abstract: We report the development of Pd(II)-catalyzed C(sp3)-H arylation of Weinreb amides. This work demonstrates the first example of using Weinreb amide as a directing group for transition metal-catalyzed C(sp3)-H activation. Both the inductive effect and… read more here.

Keywords: arylation weinreb; weinreb; catalyzed sp3; weinreb amides ... See more keywords

Pd(II)-Catalyzed Enantioselective C(sp3)–H Arylation of Cyclopropanes and Cyclobutanes Guided by Tertiary Alkylamines

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recommendations! Published in 2022 at "Journal of the American Chemical Society"

DOI: 10.1021/jacs.1c11921

Abstract: Strained aminomethyl-cycloalkanes are a recurrent scaffold in medicinal chemistry due to their unique structural features that give rise to a range of biological properties. Here, we report a palladium-catalyzed enantioselective C(sp3)–H arylation of aminomethyl-cyclopropanes and… read more here.

Keywords: cyclopropanes cyclobutanes; enantioselective sp3; tertiary alkylamines; sp3 arylation ... See more keywords

PdII-Catalyzed Site-selective β- and γ-C(sp3)-H Arylation of Primary Aldehydes Controlled by Transient Directing Groups.

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recommendations! Published in 2022 at "Journal of the American Chemical Society"

DOI: 10.1021/jacs.1c13586

Abstract: Pd(II)-catalyzed site-selective β- and γ-C(sp3)-H arylation of primary aldehydes is developed by rational design of L,X-type transient directing groups (TDG). External 2-pyridone ligands are identified to be crucial for the observed reactivity. By minimizing the… read more here.

Keywords: arylation primary; selective sp3; catalyzed site; sp3 arylation ... See more keywords
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sp3 C-H Arylation and Alkylation Enabled by the Synergy of Triplet Excited Ketones and Nickel Catalysts.

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recommendations! Published in 2018 at "Journal of the American Chemical Society"

DOI: 10.1021/jacs.8b07405

Abstract: Triplet ketone sensitizers are of central importance within the realm of photochemical transformations. Although the radical-type character of triplet excited states of diaryl ketones suggests the viability for triggering hydrogen-atom transfer (HAT) and single-electron transfer… read more here.

Keywords: nickel catalysts; triplet; excited ketones; triplet excited ... See more keywords

Pd-catalysed selective C(sp3)-H arylation and acetoxylation of alcohols.

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recommendations! Published in 2019 at "Chemical communications"

DOI: 10.1039/c9cc02911g

Abstract: A palladium catalyzed selective C(sp3)-H arylation and acetoxylation of alcohols using a practical bidentate auxiliary were developed. Masked alcohols were selectively arylated at the β-position with diverse aryl iodides for the first time. Moreover, an… read more here.

Keywords: sp3; acetoxylation; acetoxylation alcohols; arylation acetoxylation ... See more keywords