Electrochemical Arylation of Activated Olefins using a Nickel Salt as Catalyst

Electrocatalytic fluoroalkylation of olefins

“…The reactions can be run at 10 mol% nickel catalyst to afford product in moderate yields. Interestingly, the end-product is a dimer, bearing two perfluoroalkyl and two olefin synthons, unlike all previously described cases of electrocatalytic additions to olefins [1,5,[7][8][9]25]. …”

“…The last of these methods can be made catalytic in metal complex upon the introduction of a chemical reducing agent [4] or by electrochemical means [5,6]. Some of the metals capable of generating organic radicals for olefin addition chemistry via electrocatalytic reduction are [Ni(tet a)] 2+ [5], CoBr 2 (py) x [7,8], NiBr 2 (py) x [9] (tet a = 5,5,7,12,12,14-hexamethyl-1,4,-8, 11-tetra-azacyclotetradecan; py = pyridine).…”

Acrolein Diethyl Acetal: A Three‐Carbon Homologating Reagent for the Synthesis of β‐Arylpropanoates and Cinnamaldehydes by Heck Reaction Catalyzed by a Kaiser Oxime Resin Derived Palladacycle

“…[9g] ethyl 3-(4-cyanophenyl)propanoate (4c), [16] 4-chlorocinnamaldehyde (5a), [4] 4-methoxycinnamaldehyde (5f), [4] (E)-3-(1-naphthyl)propenal (5g), [9g] (E)-3-(naphthalen-2-yl)propenal (5h), [17] 4-(dimethylamino)cinnamaldehyde (5i), [4] 3-(benzyloxy)cinnamaldehyde (5j), [14] (E)-3-(pyridin-3-yl)propenal (5k), [18] and 4-(trifluoromethyl)cinnamaldehyde (5l) [19] are known compounds. -3-yl) …”

Oxidation and Reduction of Halogen‐containing Compounds

“…Catalytic processes based on the use of electrogenerated nickel(0) bipyridine complexes have been a prominent theme in the laboratories of Nédélec, Périchon, and Troupel; some of the more recent work has involved the following: (1) cross-coupling of aryl halides with ethyl chloroacetate [143], with activated olefins [144], and with activated alkyl halides [145], (2) coupling of organic halides with carbon monoxide to form ketones [146], (3) coupling of α-chloroketones with aryl halides to give α-arylated ketones [147], and (4) formation of ketones via reduction of a mixture of a benzyl or alkyl halide with a metal carbonyl [148].…”