A facile, efficient, and chemoselective synthesis of allylic amides has been developed. Allyl bromides were used as the precursors activated by silver triflate. A Ritter-type reaction readily proceeded to give various allyl amides under mild conditions. The reaction protocol was also applicable to different nucleophilic partners to give a wide range of allyl-substituted products in the absence of a base.
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http://dx.doi.org/10.1021/acs.joc.1c00480 | DOI Listing |
Sci Rep
December 2024
State Key Laboratory for Biology of Plant Disease and Insect Pests, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing, 100193, People's Republic of China.
There is a growing problem in China, whereby tomato replant disease is being affected by Fusarium spp., Meloidogyne spp., and Phytophthora spp.
View Article and Find Full Text PDFJ Am Chem Soc
December 2024
EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St. Andrews, KY16 9ST, U.K.
The [1,2]-rearrangement of allylic ammonium ylides is traditionally observed as a competitive minor pathway alongside the thermally allowed [2,3]-sigmatropic rearrangement. Concerted [1,2]-rearrangements are formally forbidden, with these processes believed to proceed through homolytic C-N bond fission of the ylide, followed by radical-radical recombination. The challenges associated with developing a catalytic enantioselective [1,2]-rearrangement of allylic ammonium ylides therefore lie in biasing the reaction pathway to favor the [1,2]-reaction product, alongside controlling a stereoselective radical-radical recombination event.
View Article and Find Full Text PDFJ Am Chem Soc
December 2024
Department of Chemistry, Pohang University of Science and Technology (POSTECH), Pohang 37673, Republic of Korea.
We report a copper-catalyzed regio-, diastereo-, and enantioselective allylic alkylation of allyl bromides using 1,1-diborylalkanes as prochiral nucleophiles. This methodology employs copper(I) bromide as a catalyst, an ()-BINOL-derived phosphoramidite as a ligand, and lithium benzoate as a crucial additive. The reaction affords enantioenriched homoallylic boronic esters possessing vicinal stereocenters in good yields and high diastereo- and enantioselectivity.
View Article and Find Full Text PDFCarbohydr Polym
February 2025
Laboratory of Applied Chemistry and Environment, Faculty of Sciences, Mohamed first University Oujda, Morocco.
Allyl Cellulose (AC) was synthesized using allyl bromide in sodium hydroxide (NaOH)/urea aqueous solution. By employing a molar ratio of 6:1 of allyl bromide/cellulose, low-degree of substitution (DS) water-soluble AC (AC) was obtained (DS = 0.67).
View Article and Find Full Text PDFJ Am Chem Soc
December 2024
Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
Catalytic asymmetric α-alkylation of simple carboxylic acid derivatives is a challenging issue due to the difficulties in achieving high catalytic efficiency and controlling the enantioselectivity. Herein, by using a copper(I)-()-DTBM-SEGPHOS complex as a catalyst and 2-acylimidazoles as pronucleophiles, a general method for the catalytic asymmetric α-alkylation of simple carboxylic acid derivatives is accomplished. Various alkyl electrophiles, including allyl bromides, benzyl bromides, propargyl bromide, and unactivated alkyl sulfonates, serve as efficient alkylation reagents.
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