Palladium(II)-Catalyzed Intramolecular Aminobromination and Aminochlorination of Olefins.

Abstract

Ring closure reactions O 0130Palladium (II)-Catalyzed Intramolecular Aminobromination and Aminochlorination of Olefins. -Optimal conditions for the title reaction are developed. The use of a stoichiometric amount of Cu(II) halide to aid in halogen transfer and catalyst oxidation leads to high yields of cyclized products. The degree of regioselectivity varies with the substrate structure. It is found that the solvent, reaction temperature, and the nature of the copper halide influence the course of the reaction. -(MANZONI, M. R.; ZABAWA, T. P.; KASI, D.; CHEMLER*, S. R.; Organometallics 23 (2004) 23, 5618-5621; Dep. Chem., State Univ. N. Y., Buffalo, NY 14260, USA; Eng.) -Klein 11-058

Crystal structure of 1-benzamido-2-chloro-1-(4-methylphenyl)-2-nitropropane, C17H17ClN2O3

“…1,2-Haloamines are important building blocks in organic, bioorganic and medicinal chemistry [1][2][3][4][5][6][7], which can be converted to aziridines [8][9], dehydroamino acids [10] and other compounds [2][3][4][5][6][7] via intra and intermolecular substitution reactions. Because the carbon-nitrogen and carbon-halogen bonds can be effectively formed in asingle process [11], the aminohalogenation of a,b-unsaturated functionalized olefins has becomeone of the most efficient method to get 1,2-haloamines derivatives.…”

Highly Regio‐ and Stereoselective Synthesis of α‐(N‐Alkyl‐N‐p‐toluenesulfonyl)‐β‐Bromo‐Ketones via Ni(OAc)2‐Catalyzed Aminobromination of Chalcones

“…The aminohalogenation and related reactions using functionalized olefins have been interesting topics in organic synthesis because the resulting vicinal haloamines are important building blocks in organic, bioorganic, and medicinal chemistry (1–14). The resulting vicinal haloamines from these reactions can readily undergo both intramolecular and intermolecular processes to afford aziridines (15–17), dehydroamino acids (18), and other important compounds (1–14). Although many synthetic approaches to vicinal haloamines have been developed using α,β‐unsaturated carbonyls as substrates (19–27), the development of highly regio‐ and stereoselective aminohalogenation still remains challenging.…”