143023-64-7

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 585533-41-1 C₁₁H₁₃NO₃ 
• 79-24-3 Nitroethane 
• 104-55-2 3-phenyl-propenal 
• 60593-26-2 (1-nitroethyl)-phosphonic acid diethyl ester 

Downstream Products

• 3042-21-5 2-methyl-5-phenyl-1H-pyrrole 
• 1397266-43-1 (E,3S,4R)-4-nitro-1-phenylpent-1-en-3-yl ethanethioate 
• 877-94-1 phenyl-5 pentene-4 one-2 
• 1402405-59-7 (E)-1,2,3,4,5-pentafluoro-6-(1-nitro-4-phenylbut-3-en-2-yl)benzene 
• 10521-97-8 5-phenyl-pent-3-en-2-one 
• 1054487-20-5 (-)-(S,E)-5-phenyl-hex-3-en-2-one 
• 83542-41-0 (E)-3-methyl-5-phenyl-4-pentene-2-one 
• 91711-97-6 (E)-(5RS)-5-phenylhex-3-en-2-one 

Relevant academic research and scientific papers

A Synthetic Methodology for Pyrroles from Nitrodienes

Palladium complexes containing the ligand 4,7-dimethoxy-1,10-phenanthroline have been used to catalyze the reductive cyclization of nitrodienes using carbon monoxide as the reductant to give pyrroles. Carbon dioxide was the only stoichiometric byproduct of the reaction. The yields were good and the starting materials can be easily synthesized in two steps by a cross-aldol condensation reaction followed by a Henry reaction. Different substitution patterns are tolerated by this novel synthetic strategy.

Substituted pyrrole synthesis from nitrodienes

Though the Cadogan-Sundberg approach has been employed to synthesize a variety of indole and carbazole derivatives from nitroarenes, surprisingly, very little is reported for making pyrroles using the same approach from non-arene nitrodienes. Herein, we report a general method to synthesize substituted pyrroles, in one step with modest yields, from nitrodienes using triphenylphosphine in the presence of an Mo catalyst, bis(acetylaceto)dioxomolybdenum (VI). To shed light on the mechanism of this reaction, we performed DFT calculations using uB3LYP/6-31+G(d) basis set and observed that the reaction favors a path through a nitrene intermediate.

One-pot solid phase synthesis of (E)-nitroalkenes

An efficient one-pot protocol for the synthesis of (E)-nitroalkenes by reaction of aldehydes and nitroalkanes in the presence of polymer-bound triphenylphosphine, iodine and imidazole is described. Although the reaction works with similar efficiency with triphenylphosphine and its polymer-bound version, easy removal of the unwanted polymer-bound triphenylphosphine oxide and its recovery as triphenylphosphine provide the edge for practical application of the method.

Enantio- and regioselective conjugate addition of organometallic reagents to linear polyconjugated nitroolefins

The copper-catalysed conjugate addition of trialkylaluminium and dialkylzinc reagents to polyconjugated nitroolefins (nitrodiene and nitroenyne derivatives) is reported. A reversed Josiphos ligand L7 allows for the selective 1,4- or 1,6-addition with high enantioselectivities. Copyright

A New Method for the Preparation of Conjugated Nitro Olefins

Condensation of 1-nitroalkanephosphonates with carbonyl compounds affords a new and facile method for the preparation of conjugated nitro olefins.