Intramolecular Borylation via Sequential B-Mes Bond Cleavage for the Divergent Synthesis of B,N,B-Doped Benzo[4]helicenes was written by Knoeller, Julius A.;Meng, Guoyun;Wang, Xiang;Hall, David;Pershin, Anton;Beljonne, David;Olivier, Yoann;Laschat, Sabine;Zysman-Colman, Eli;Wang, Suning. And the article was included in Angewandte Chemie, International Edition in 2020.Synthetic Route of C8H8Br2 This article mentions the following:
New sym. and unsym. B,N,B-doped benzo[4]helicenes 3–6闁?strong>a/b have been achieved in good yields, using a three-step process, starting from N(tolyl)3 in a highly divergent manner (7 examples). A borinic acid functionalized 1,4-B,N-anthracene 1 was found to display unprecedented reactivity, acting as a convenient and highly effective precursor for selective formation of bromo-substituted B,N,B-benzo[4]helicenes 2闁?strong>a/2闁?strong>b via intramol. borylation and sequential B-Mes bond cleavage in the presence of BBr3. Subsequent reaction of 2闁?strong>a/2闁?strong>b with Ar-Li provided a highly effective toolbox for the preparation of sym./unsym. functionalized B,N,B-helicenes. Their high photoluminescence quantum yields along with the small 闁剧粯婀?sub>ST suggest their potential as thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs). In the experiment, the researchers used many compounds, for example, 2,5-Dibromo-1,3-dimethylbenzene (cas: 100189-84-2Synthetic Route of C8H8Br2).
2,5-Dibromo-1,3-dimethylbenzene (cas: 100189-84-2) 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. 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 C8H8Br2
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary