Organocatalytic Asymmetric Dearomatizing Hetero-Diels-Alder Reaction of Nonactivated Arenes was written by Li, Kai;Huang, Shengli;Liu, Tianyu;Jia, Shiqi;Yan, Hailong. And the article was included in Journal of the American Chemical Society in 2022.Quality Control of 1-Bromopyrrolidine-2,5-dione This article mentions the following:
Nonactivated arenes, such as benzene derivatives, are chem. inert due to their intrinsic aromaticity and low polarity. The catalytic asym. dearomatization (CADA, coined by You and co-workers) of the nonactivated arenes represents a formidable challenge. Herein, the authors demonstrate an organocatalytic asym. dearomatizing hetero-Diels-Alder reaction of benzene derivatives The tunable regioselectivity of this strategy allowed delivery of a diversity of stereochem. complex polycyclic compounds, e.g., I, and oxahelicenes, e.g., II, with excellent stereoselectivity. The high complexity and three-dimensionality of the products were crucial for their potential applications in materials science and drug discovery. Mechanistic studies suggested that this reaction proceeded through a chiral tetra-substituted vinylidene ortho-quinone methide (VQM) intermediate, which was extremely active to overcome the loss of aromaticity of benzene derivatives with concomitant chirality transfer. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Quality Control of 1-Bromopyrrolidine-2,5-dione).
1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbon–bromine bond is electrophilic in nature. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Quality Control of 1-Bromopyrrolidine-2,5-dione
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary