Jstevens

Organophotoredox Hydrodefluorination of Trifluoromethylarenes with Translational Applicability…

Abstract: Molecular editing such as insertion, deletion, and single atom exchange in highly functionalized compounds is an aspirational goal for all chemists. Here, we disclose a photoredox protocol for the replacement of a single fluorine atom with hydrogen in electron-deficient trifluoromethylarenes including complex drug molecules. A robustness screening experiment shows that this reductive defluorination tolerates…

A Unified and Practical Method for Carbon-Heteroatom CrossCoupling via Nickel/Photo Dual Catalysis

Abstract: While carbon-heteroatom cross coupling reactions have been extensively studied, many methods are specific and limited to a particular set of substrates or functional groups. Reported here is a general method that allows for C-O, C-N and C-S cross coupling reactions under one general set of conditions. We propose that an energy transfer pathway, in…

Organocatalytic C–H fluoroalkylation of commodity polymers

Abstract: Post-polymerization modification of commodity plastics diversifies their material properties and expands their potential applications. The thermal and chemical stability of polymers that contain aromatic rings, which represent a high-volume class of materials, makes it challenging to add functionality while retaining the molar mass (Mn) and molecular weight distribution (MWD) of the original polymer. Herein,…

Dimethyl‐dihydroacridines as Photocatalysts in the Organocatalyzed ATRP of Acrylate Monomers

Abstract: Development of photocatalysts (PCs) with diverse properties has been essential in advancement of organocatalyzed atom transfer radical polymerization (O‐ATRP). In this work, dimethyl‐dihydroacridines are presented as a new family of organic PCs, for the first time enabling controlled polymerization of challenging acrylate monomers via O‐ATRP. Structure‐property relationships for seven PCs are established, demonstrating tunable…

Energy Transfer to Ni-amine Complexes in Dual Catalytic, Light-driven C–N Cross-Coupling Reactions

Abstract: Dual catalytic light-driven cross coupling methodologies utilizing a Ni(II) salt with a photocatalyst (PC) have emerged as promising methodologies to forge aryl C–N bonds under mild conditions. The recent discovery that the PC can be omitted and the Ni(II) complex directly photoexcited suggests that the PC may perform energy transfer (EnT) to the Ni(II)…