Substitution Reaction of Nitro Group on α-Nitrostyrene by Organozinc Halides Under Microwave Irradiation

Denitrative Cross-Couplings of Nitrostyrenes

“…Although each proposal differs in detail, the main three characteristic steps feature in all proposals. Firstly, carbon- or heteroatom-centered radical 4 is generated in situ by various methods from precursors 6 – 33 [ 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 ]. These include a thermal homolytic cleavage of labile bonds, metal-catalyzed and photochemically initiated processes.…”

“…Although the described substrate scope was relatively narrow, seven examples were reported, and the reaction proceeded smoothly at ambient temperature, with excellent chemical yields, ranging from 81 to 89%. A year later, in 1999, the same research group reported a modified variant of the coupling [ 20 ]. Simple and functionalized organozinc iodides underwent the cross-coupling under microwave irradiation.…”

ChemInform Abstract: Organometallic Chemistry. Part 2. Transition Metals in Organic Synthesis: Stoichiometric Applications

“…in under 10 min on reaction with pentylzinc iodide. 85 Ultra-reactive Zn powder is prepared by sonoelectroreduction of ZnCl 2 in aqueous NH 4 Cl. Alternating pulses of current and ultrasound are employed to generate extremely ¢ne powders (nanopowders) and the pulse duration and interval can be used to control the particle size.…”

Triethylaluminum- or Triethylborane-Induced Free Radical Reaction of Alkyl Iodides and α,β-Unsaturated Compounds

“…Reactions of β-nitrostyrenes with organometallic reagents such as dialkylzinc1a or organozinc halides, 1b,c t -BuHgX/KI, organomanganese, trialkylaluminum or dialkylaluminum chloride, trialkylgallium, and Grignard reagents lead to the generation of alkenes and/or nitroalkanes or halooximes. A previous study found that medium to high yields of alkenes can be generated when ( E )-β-nitrostyrenes 1 are reacted with triethylborane in a THF solution under reflux in the presence of a trace of oxygen or by photolysis in the presence of tert -butyl peroxide as a radical initiator .…”