Regioselective Bromine/Magnesium Exchange for the Selective Functionalization of Polyhalogenated Arenes and Heterocycles
作者:Alexandre Desaintjean、Tobias Haupt、Leonie J. Bole、Neil R. Judge、Eva Hevia、Paul Knochel
DOI:10.1002/anie.202012496
日期:2021.1.18
toluene enables efficient and regioselective Br/Mg exchanges with various dibromo‐arenes and ‐heteroarenes under mild reaction conditions and provides bromo‐substituted magnesium reagents. Assessing the role of Lewis donor additives in these reactions revealed that N,N,N′,N′′,N′′‐pentamethyldiethylenetriamine (PMDTA) finely tunes the regioselectivity of the Br/Mg exchange on dibromo‐pyridines and quinolines
facile exterior alkylation of the polyaromatic framework leads to a moderately fluorescent tube (R=‐OC10H21; ΦF=20 %) in the solidstate. The emission intensity of the solid‐state alkyl‐substituted tube is remarkably enhanced upon heating (up to 1.6 times, ΦF=31 %) as well as doping with fluorescent dyes (up to 4.2 times, ΦF=83 %) through efficient energy transfer.