The addition of nucleophilic organometallic species onto generated azabicyclobutanes enables the selective formation of 3-arylated azetidine intermediates through strain-release. Single pot strategies were further developed for the -arylation of resulting azetidines, employing either SAr reactions or Buchwald-Hartwig couplings.
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http://dx.doi.org/10.1039/d1cc07053c | DOI Listing |
Chem Commun (Camb)
June 2024
Key Laboratory of Catalysis and Energy Materials Chemistry of Ministry of Education & Hubei Key Laboratory of Catalysis and Materials Science, School of Chemistry and Materials Science, South-Central MinZu University, Wuhan 430074, China.
Polysubstituted acrylamides are ubiquitous in bioactive molecules and natural products. However, synthetic methods for the assembly of these important motifs remain underdeveloped. Herein, we report the expedient synthesis of structurally diverse and synthetically challenging polysubstituted acrylamides from readily available aromatic amines, cyclopropenones (CpOs), and aryl halides the synergistic merging of nucleophilic phosphine-mediated amidation and palladium-catalyzed C-H arylation.
View Article and Find Full Text PDFChem Commun (Camb)
February 2022
Department of Chemistry and Pharmacy, Ludwig-Maximilians-Universität München, Butenandtstraße 5-13, 81377 Munich, Germany.
The addition of nucleophilic organometallic species onto generated azabicyclobutanes enables the selective formation of 3-arylated azetidine intermediates through strain-release. Single pot strategies were further developed for the -arylation of resulting azetidines, employing either SAr reactions or Buchwald-Hartwig couplings.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2022
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
The identification of spiro N-heterocycles as scaffolds that display structural novelty, three-dimensionality, beneficial physicochemical properties, and enable the controlled spatial disposition of substituents has led to a surge of interest in utilizing these compounds in drug discovery programs. Herein, we report the strain-release-driven Friedel-Crafts spirocyclization of azabicyclo[1.1.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
October 2021
School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK.
The ring-opening of 3-aminocyclobutanone oximes enables easy generation of primary alkyl radicals, capable of undergoing an unprecedented strain-release, desulfonylative radical Truce-Smiles rearrangement, providing divergent access to valuable 1,3 diamines and unnatural β-amino acids. Characterized by mild conditions and wide scope of migrating species, this protocol allows the modular assembly of sp -aryls under transition metal-free, room-temperature conditions.
View Article and Find Full Text PDFChem Sci
April 2021
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania 231 South 34th Street Philadelphia PA USA
We report a 3-component reaction between -benzyl ketimines, [1.1.1]propellane, and pinacol boronates to generate benzylamine bicyclo[1.
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