Bole, Leonie J. published the artcileEnhancing Metalating Efficiency of the Sodium Amide NaTMP in Arene Borylation Applications, HPLC of Formula: 91-16-7, the publication is Angewandte Chemie, International Edition (2022), 61(26), e202204262, database is CAplus and MEDLINE.
Though LiTMP (TMP = 2,2,6,6-tetramethylpiperidide) is a commonly used amide, surprisingly the heavier NaTMP has hardly been utilized. Here, by mixing NaTMP with tridentate donor PMDETA (N,N,N’,N”,N”-pentamethyldiethylenetriamine), we provide structural, and mechanistic insights into the sodiation of non-activated arenes (e.g. anisole and benzene). While these reactions are low yielding, adding B(OiPr)3 has a profound effect, not only by intercepting the CAr-Na bond, but also by driving the metalation reaction towards quant. formation of more stabilized sodium aryl boronates. Demonstrating its metalating power, regioselective C2-metalation/borylation of naphthalene has been accomplished contrasting with single-metal based protocols which are unselective and low yielding. Extension to other arenes allows for in situ generation of aryl boronates which can then directly engage in Suzuki-Miyaura couplings, furnishing a range of biaryls in a selective and efficient manner.
Angewandte Chemie, International Edition published new progress about 91-16-7. 91-16-7 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether,Inhibitor,Inhibitor,Inhibitor, name is 1,2-Dimethoxybenzene, and the molecular formula is C8H10O2, HPLC of Formula: 91-16-7.
Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem