C(sp3)-Arylation by Conformationally Accelerated Intramolecular Nucleophilic Aromatic Substitution (SNAr)
Sign Up to like & getrecommendations! 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.
Sign Up to like & getrecommendations! 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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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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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
Pd/Cu-Catalyzed Cascade C(sp3)-H Arylation and Intramolecular C-N Coupling: A One-Pot Synthesis of 3,4-2 H-Quinolinone Skeletons.
Sign Up to like & getrecommendations! 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.
Sign Up to like & getrecommendations! 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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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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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
sp3 C-H Arylation and Alkylation Enabled by the Synergy of Triplet Excited Ketones and Nickel Catalysts.
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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.
Sign Up to like & getrecommendations! 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
Directed C(sp3)–H arylation of tryptophan: transformation of the directing group into an activated amide
Sign Up to like & getrecommendations! Published in 2019 at "Chemical Science"
DOI: 10.1039/c9sc03440d
Abstract: The aminoquinoline-directed C–H activation was used to synthezise unnatural tryptophans for solid phase peptide synthesis for the first time. read more here.
Keywords: transformation directing; sp3 arylation; arylation tryptophan; directed sp3 ... See more keywords