Bromonitroalkenes are useful molecules in synthetic organic chemistry. They are mainly prepared from nitroalkenes bromination reactions. In this review, the application of bromonitroalkenes as partners in the reaction with a diversity of mono- and bi-functional molecules, including aldehydes and ketones, active methylene compounds, 1,2-dicarbonyls, enamines, enols, electron-rich arenes, amidines, azomethine ylides, azirines, diazo compounds, and many others, is reviewed. By using these substrates, various biologically active scaffolds, such as heterocycles, carbocycles, spirocycles, polycyclic systems, natural products, and other useful acyclic compounds, were prepared. In addition, due to their dielectrophilic character, electrophilic and nucleophilic character, and ability to participate in cycloaddition reactions, bromonitroalkenes were efficiently applied in asymmetric cascade/domino/tandem reactions catalyzed by chiral catalysts. In this manuscript, around 55 papers are summarized and discussed during the years 2000-2023.
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Bromonitroalkenes as efficient intermediates in organic synthesis.
Org Biomol Chem
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Department of Chemistry, Sharif University of Technology, Tehran 11155-9516, Iran.
Bromonitroalkenes are useful molecules in synthetic organic chemistry. They are mainly prepared from nitroalkenes bromination reactions. In this review, the application of bromonitroalkenes as partners in the reaction with a diversity of mono- and bi-functional molecules, including aldehydes and ketones, active methylene compounds, 1,2-dicarbonyls, enamines, enols, electron-rich arenes, amidines, azomethine ylides, azirines, diazo compounds, and many others, is reviewed.
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Middle East Technical University, Department of Chemistry, 06800, Çankaya, Ankara, Turkey.
Squaramide/cinchona alkaloid-derived bifunctional organocatalysts are in high demand in asymmetric transformations. Bifunctional quinine-derived sterically encumbered squaramide (H-bond donor) organocatalysts were used to catalyze the asymmetric Friedel-Crafts/S2 type domino reaction of ()-α-bromonitroalkenes and α/β-naphthols and phenol derivatives to generate enantiomerically enriched dihydronaphthofuran (DHN) and dihydrobenzofuran (DHB) derivatives, respectively. The target adducts were obtained in up to >99% ee under mild conditions with a relatively low catalyst loading (5 mol%) compared to the methods known in the literature.
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State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, People's Republic of China.
A highly chemoselective [2+1] annulation of α-alkylidene pyrazolones with α-bromonitroalkenes has been achieved under mild conditions. α-Alkylidene pyrazolones were unprecedentedly used as a C1 synthon to participate in annulation reactions, providing access to diverse vinylcyclopropane-based pyrazolone products. In addition, a spectrum of pharmaceutically interesting pyrazole-fused pyranone oximes could be rapidly obtained through a [2+1] annulation/rearrangement sequential process.
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Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400 076, India.
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Institute of Exact Sciences, Department of Chemistry, Federal University of Minas Gerais, CEP, 31270-901, Belo Horizonte, MG, Brazil. Electronic address:
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