A copper-catalyzed reaction between 2-bromo-benzothioamides and S or Se involving sulfur rearrangement is reported, enabling access to benzodithioles and benzothiaselenoles in the presence of CsCO. In the absence of S or Se, the reaction affords dibenzodithiocines via two consecutive C(sp)-S Ullmann couplings.
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http://dx.doi.org/10.1021/acs.orglett.0c00907 | DOI Listing |
Chem Asian J
November 2024
Department of Chemistry, Faculty of Science, Niigata University, Nishi-ku, Niigata, 950-2181, Japan.
Despite the significant development and extensive application of phthalocyanine and related azaporphyrins, little attention has been paid to meso-N-substituted azaporphyrinoids. Here, we report new derivatives of 5,10,20-triaryl-5,15-diazaporphyrinoids (ArDAP), which are reversibly redox-switchable between the 18π- and 19π-electron state. Four kinds of metal(II) complexes and free bases of ArDAP were prepared by metal-templated cyclization of metal(II) complexes of 5,10,15-triaryl-10-azabiladiene-ac with sodium azide or copper-catalyzed N-phenylation of 10,20-diaryl-5,15-diazaporphyrins (ArDAP) with diphenyliodonium hexafluorophosphate.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
October 2024
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
Despite extensive efforts to develop γ-lactamization reactions for pyrrolidinone synthesis using either cyclometallation, C-H insertion, or radical C-H abstraction strategies, γ-lactamization reactions of aliphatic amides using practical catalysts and common protecting groups remain extremely rare. Herein we report copper-catalyzed γ-C(sp)-H lactamization and iminolactonization of tosyl-protected aliphatic amides using inexpensive Selectfluor as the sole oxidant. A switchable selectivity of γ-lactams or γ-iminolactones can be obtained by using two different sets of reaction conditions.
View Article and Find Full Text PDFNat Commun
August 2024
School of Food and Biological Engineering, Hefei University of Technology, Hefei, China.
CF-containing compounds hold significant potential in drug discovery, organic synthesis, and materials science. However, synthesizing various CF-containing building blocks from a single compound remains challenging. Here, we present a Cu-catalyzed, switchable defluoroborylation and hydrodefluorination of trifluoromethylated alkynes, yielding four types of CF-containing compounds.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
August 2023
School of Chemistry and Chemical Engineering, Queen's University Belfast, David Keir Building, Stranmillis Road, Belfast, BT9 5AG, UK.
To reach their potential as mimics of the dynamic molecules present in biological systems, foldamers must be designed to display stimulus-responsive behavior. Here we report such a foldamer architecture based on alternating pyridine-diketopiperazine linkers. Epimerization is conveniently prevented through a copper-catalyzed coupling protocol.
View Article and Find Full Text PDFChem Commun (Camb)
July 2023
Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai, 200237, PR China.
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