Site-Selective, Remote sp3 C-H Carboxylation Enabled by the Merger of Photoredox and Nickel Catalysis was written by Sahoo, Basudev;Bellotti, Peter;Julia-Hernandez, Francisco;Meng, Qing-Yuan;Crespi, Stefano;Koenig, Burkhard;Martin, Ruben. And the article was included in Chemistry – A European Journal in 2019.Synthetic Route of C9H11BrO This article mentions the following:
In the presence of (bipyridine)nickel(II) bromides and the photoredox catalyst CzIPN, arylalkyl bromides such as PhCH2CH2Br underwent regioselective photochem. carboxylation with CO2 to yield carboxylic acids such as α-methylphenylacetic acid. Alkyl halides in the presence of CzIPN and a related (bipyridine)nickel(II) bromide underwent regioselective carboxylation to give unbranched carboxylic acids; a mixture of bromoheptanes reacted to yield octanoic acid regioselectively. Exptl. and computational studies of the reaction mechanism were performed; a mechanism involving dynamic displacement of the catalyst throughout the alkyl chain is proposed. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Synthetic Route of C9H11BrO).
1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Synthetic Route of C9H11BrO
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary