Rhodium-Catalyzed C-H Activation of Phenacyl Ammonium Salts Assisted by an Oxidizing C-N Bond: A Combination of Experimental and Theoretical Studies was written by Yu, Songjie;Liu, Song;Lan, Yu;Wan, Boshun;Li, Xingwei. And the article was included in Journal of the American Chemical Society in 2015.SDS of cas: 80480-15-5 The following contents are mentioned in the article:
Rh(III)-catalyzed C-H activation assisted by an oxidizing directing group has evolved to a mild and redox-economic strategy for the construction of heterocycles. Despite the success, these coupling systems are currently limited to cleavage of an oxidizing N-O or N-N bond. Cleavage of an oxidizing C-N bond, which allows for complementary carbocycle synthesis, is unprecedented. α-Ammonium acetophenones with an oxidizing C-N bond were designed as substrates for Rh(III)-catalyzed C-H activation under redox-neutral conditions. The coupling with α-diazo esters afforded benzocyclopentanones, and the coupling with unactivated alkenes such as styrenes and aliphatic olefins gave ortho-olefinated acetophenoes. In both systems the reactions proceeded with a broad scope, high efficiency, and functional group tolerance. Also, efficient 1-pot coupling of diazo esters was realized starting from α-bromoacetophenones and triethylamine. The reaction mechanism for the coupling with diazo esters was studied by a combination of exptl. and theor. methods. In particular, three distinct mechanistic pathways were scrutinized by DFT studies, which revealed that the C-H activation occurs via a C-bound enolate-assisted concerted metalation-deprotonation mechanism and is rate-limiting. In subsequent C-C formation steps, the lowest energy pathway involves two rhodium carbene species as key intermediates. This study involved multiple reactions and reactants, such as 2-Bromo-1-(pyren-1-yl)ethanone (cas: 80480-15-5SDS of cas: 80480-15-5).
2-Bromo-1-(pyren-1-yl)ethanone (cas: 80480-15-5) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.SDS of cas: 80480-15-5
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary