96409-47-1Relevant academic research and scientific papers
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.
Catalytic Deprotonative α-Formylation of Heteroarenes by an Amide Base Generated in Situ from Tetramethylammonium Fluoride and Tris(trimethylsilyl)amine
Shigeno, Masanori,Fujii, Yuki,Kajima, Akihisa,Nozawa-Kumada, Kanako,Kondo, Yoshinori
, p. 443 - 451 (2019/04/30)
Heteroarene formylations in DMF solution proceed in the presence of an amide base catalyst generated in situ from tetramethylammonium fluoride (TMAF) and tris(trimethylsilyl)amine (N(TMS)3). The reaction proceeds at room temperature and has an operationally simple procedure. Various heteroarenes, including benzothiophene, thiophene, benzothiazole, oxazole, and indole derivatives, can be formylated with high functional group tolerance.
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
Metal-free deprotonative functionalization of heteroaromatics using organic superbase catalyst
Hirono, Yutaro,Kobayashi, Koji,Yonemoto, Misato,Kondo, Yoshinori
supporting information; experimental part, p. 7623 - 7624 (2010/12/19)
Metal-free deprotonative functionalization of heteroaromatic compounds was achieved using an organic superbase catalyst; an organosilicon additive such as trimethylsilylpropyne was employed for activating the catalytic cycle of 1,2-addition to carbonyl compounds.
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.
General Reactivity of 2-Lithiobenzothiazole to Various Electrophiles and the Use as a Formyl Anion Equivalent in the Synthesis of α-Hydroxy Carbonyl Compounds
Chikashita, Hidenori,Ishibaba, Megumi,Ori, Keiji,Itoh, Kazuyoshi
, p. 3637 - 3648 (2007/10/02)
The reaction of 2-lithiobenzothiazole with a variety of electrophiles such as aldehydes, ketones, carboxylic esters, lactones, nitriles, and amides afforded the expected addition and substitution products.Trimethylsilyl chloride readily reacted with the b
REACTION OF 2-LITHIOBENZOTHIAZOLE WITH ELECTROPHILES AND A SYNTHESIS OF α-HYDROXY ALDEHYDES AND KETONES
Chikashita, Hidenori,Itoh, Kazuyoshi
, p. 295 - 300 (2007/10/02)
The reaction of 2-lithiobenzothiazole with a variety of electrophiles, exept for alkyl halides and styrene oxide, could be effectively accomplished to give the expected products in high yields.The adducts of lithiobenzothiazole to carbonyl compounds could
