27172-99-2Relevant academic research and scientific papers
Electrochemical oxidative: Z -selective C(sp2)-H chlorination of acrylamides
Coles, Simon J.,Hareram, Mishra Deepak,Harnedy, James,Morrill, Louis C.,Tizzard, Graham J.
supporting information, p. 12643 - 12646 (2021/12/07)
An electrochemical method for the oxidative Z-selective C(sp2)-H chlorination of acrylamides has been developed. This catalyst and organic oxidant free method is applicable across various substituted tertiary acrylamides, and provides access to a broad range of synthetically useful Z-β-chloroacrylamides in good yields (22 examples, 73% average yield). The orthogonal derivatization of the products was demonstrated through chemoselective transformations and the electrochemical process was performed on gram scale in flow.
Visible-Light-Mediated Heterocycle Functionalization via Geometrically Interrupted [2+2] Cycloaddition
Alegre-Requena, Juan V.,Mekereeya, Aroonroj,Paton, Robert S.,Popescu, Mihai V.,Smith, Martin D.
supporting information, p. 23020 - 23024 (2020/10/15)
The [2+2] photocycloaddition is the most valuable and intensively investigated photochemical process. Here we demonstrate that irradiation of N-acryloyl heterocycles with blue LED light (440 nm) in the presence of an IrIII complex leads to efficient and high yielding fused γ-lactam formation across a range of substituted heterocycles. Quantum calculations show that the reaction proceeds via cyclization in the triplet excited state to yield a 1,4-diradical; intersystem crossing leads preferentially to the closed shell singlet zwitterion. This is geometrically restricted from undergoing recombination to yield a cyclobutane by the planarity of the amide substituent. A prototropic shift leads to the observed bicyclic products in what can be viewed as an interrupted [2+2] cycloaddition.
Direct ortho-thiolation of arenes and alkenes by nickel catalysis
Lin, Cong,Li, Danyang,Wang, Binjie,Yao, Jinzhong,Zhang, Yuhong
supporting information, p. 1328 - 1331 (2015/03/14)
The direct thiolation of arenes and alkenes with diaryl disulfides was developed by nickel catalysis. The reaction displayed exceptional compatibility with a wide range of functional groups to regioselectively give the diaryl sulfides and alkenyl sulfides in high yields.
The diazo route to diazonamide A: Studies on the tyrosine-derived fragment
Palmer, Francine N.,Lach, Franck,Poriel, Cyril,Pepper, Adrian G.,Bagley, Mark C.,Slawin, Alexandra M. Z.,Moody, Christopher J.
, p. 3805 - 3811 (2007/10/03)
Various approaches to the tyrosine-derived fragment of the marine secondary metabolite diazonamide A are described. Initial efforts were focused on the originally proposed structure of the natural product, and a feasibility study established that a model
The Chemistry of Aryllead Tricarboxylates. Synthesis of Some α-Aryl α,β-Unsaturated Carbonyl Compounds
Kopinski, Richard P.,Pinhey, John T.
, p. 311 - 316 (2007/10/02)
The treatment of 4-benzoyltetrahydrofuran-2,3-dione (2a) with 2 equiv. of phenyllead triacetate (3a) in chloroform gives 1,2-diphenylpropenone (4a) in excellent yield.This reaction has been investigated with a number of similar derivatives of tetrahydrofuran-2,3-dione and a number of aryllead triacetates.It has been found to be very sensitive to the nature of the substituent at C4, and it would appear to be limited to the synthesis of α-methylene carbonyl compounds since a 5-methyl substituent inhibits the reaction.
