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Resolving Conflicting Mechanisms for Photoredox Allylic sp-CH Arylation Using Deuterium-Labeling and Isotope Effects.
ACS Catal
June 2024
Department of Chemistry, Binghamton University, Vestal, New York 13850, United States.
Two conflicting mechanisms have emerged for the direct arylation of allylic C-H bonds enabled by the combined use of thiol and photoredox catalysis. In the original report ( , , 74-77), a radical coupling step-between a radical anion of an arene and an allylic radical-is proposed to be the key C-C bond-forming step. A recent mechanistic study (.
View Article and Find Full Text PDFCopper-Phosphido Catalysis: Enantioselective Addition of Phosphines to Cyclopropenes.
Angew Chem Int Ed Engl
September 2023
Department of Medicinal Chemistry, GSK, 1250 S. Collegeville Rd, 19426, Collegeville, PA, USA.
We describe a copper catalyst that promotes the addition of phosphines to cyclopropenes at ambient temperature. A range of cyclopropylphosphines bearing different steric and electronic properties can now be accessed in high yields and enantioselectivities. Enrichment of phosphorus stereocenters is also demonstrated via a Dynamic Kinetic Asymmetric Transformation (DyKAT) process.
View Article and Find Full Text PDFStereospecific Nickel-Catalyzed Cross-Electrophile Coupling Reaction of Alkyl Mesylates and Allylic Difluorides to Access Enantioenriched Vinyl Fluoride-Substituted Cyclopropanes.
ACS Catal
April 2023
Department of Chemistry, University of California, Irvine, California 92697, United States.
Cross-electrophile coupling reactions involving direct C-O bond activation of unactivated alkyl sulfonates or C-F bond activation of allylic -difluorides remain challenging. Herein, we report a nickel-catalyzed cross-electrophile coupling reaction between alkyl mesylates and allylic -difluorides to synthesize enantioenriched vinyl fluoride-substituted cyclopropane products. These complex products are interesting building blocks with applications in medicinal chemistry.
View Article and Find Full Text PDFBirds of a Feather Get High Together: A Reconceptualization of the Social Bond with Latent Class Analysis and a Test with Different Forms of Drug Use.
Am J Crim Justice
November 2022
Georgia Southern University, Statesboro, GA USA.
Social bond theory has received significant empirical support in examinations of drug use for decades. However, research utilizing the theory has often been fragmented and has not incorporated all four dimensions of the social bond. Additionally, much of this research has collapsed drug use into categories rather than examining specific forms of drug use.
View Article and Find Full Text PDFMechanism and Origin of Remote Stereocontrol in the Organocatalytic Enantioselective Formal C(sp)-H Alkylation Using Nitroalkanes as Alkylating Agents.
J Am Chem Soc
September 2022
Department of Chemistry, Binghamton University, Binghamton, New York 13902, United States.
Experimental C kinetic isotope effects (KIEs) and density functional theory (DFT) calculations are used to evaluate the mechanism and origin of enantioselectivity in the formal C(sp)-H alkylative desymmetrization of cyclopentene-1,3-diones using nitroalkanes as the alkylating agent. An unusual combination of an inverse (∼0.980) and a normal (∼1.
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