96409-47-1Relevant articles and documents
Preparation of Functionalized Aryl, Heteroaryl, and Benzylic Potassium Organometallics Using Potassium Diisopropylamide in Continuous Flow
Harenberg, Johannes H.,Knochel, Paul,Weidmann, Niels
supporting information, p. 12321 - 12325 (2020/05/04)
We report the preparation of lithium-salt-free KDA (potassium diisopropylamide; 0.6 m in hexane) complexed with TMEDA (N,N,N′,N′-tetramethylethylenediamine) and its use for the flow-metalation of (hetero)arenes between ?78 °C and 25 °C with reaction times between 0.2 s and 24 s and a combined flow rate of 10 mL min?1 using a commercial flow setup. The resulting potassium organometallics react instantaneously with various electrophiles, such as ketones, aldehydes, alkyl and allylic halides, disulfides, Weinreb amides, and Me3SiCl, affording functionalized (hetero)arenes in high yields. This flow procedure is successfully extended to the lateral metalation of methyl-substituted arenes and heteroaromatics, resulting in the formation of various benzylic potassium organometallics. A metalation scale-up was possible without further optimization.
Organocatalytic deprotonative functionalization of C(sp2)-H and C(sp3)-H bonds using in situ generated onium amide bases
Inamoto, Kiyofumi,Okawa, Hitomi,Taneda, Hiroshi,Sato, Maomi,Hirono, Yutaro,Yonemoto, Misato,Kikkawa, Shoko,Kondo, Yoshinori
supporting information, p. 9771 - 9773,3 (2020/08/31)
Onium amides, generated in situ from the combination of aminosilanes and onium fluorides (R4PF, R4NF), are employed for the first time as bases for catalytic deprotonative functionalization of C(sp 2)-H and activated C(sp
New mixed Li/Mg and Li/Mg/Zn amides for the chemoselectlve metallation of arenes and heteroarenes
Rohbogner, Christoph J.,Wunderlich, Stefan H.,Clososki, Giuliano C.,Knochel, Paul
experimental part, p. 1781 - 1795 (2009/09/05)
New mixed Li/Mg and Li/Mg/Zn amides have been synthesized starting from readily prepared secondary amines. They allow a highly chemoselective directed magnesiation or zincation of various polyfunctional aromatics and heteroaromatics. The kinetic basicity, solubility and stability of these new bases have been compared with those of the corresponding 2,2,6,6- tetramethylpiperamide-derived bases. Wiley-VCH Verlag GmbH & Co. KGaA.