365448-17-5Relevant academic research and scientific papers
Preparation of Polyfunctional Naphthyridines by Cobalt-Catalyzed Cross-Couplings of Halogenated Naphthyridines with Magnesium and Zinc Organometallics
Greiner, Robert,Ziegler, Dorothée S.,Cibu, Denise,Jakowetz, Andreas C.,Auras, Florian,Bein, Thomas,Knochel, Paul
, p. 6384 - 6387 (2017)
CoCl2 (5%) catalyzes cross-couplings of various halogenated naphthyridines with alkyl- and arylmagnesium halides. Also, arylzinc halides undergo smooth cross-couplings with various naphthyridines in the presence of CoCl2·2LiCl (5%) a
Expedient Preparation of Aryllithium and Arylzinc Reagents from Aryl Chlorides Using Lithium 4,4′-Di- tert -Butylbiphenylide and Zinc(II) Chloride
Shen, Zhi-Liang,Sommer, Korbinian,Knochel, Paul
, p. 2617 - 2630 (2015/09/01)
We report an efficient method for the preparation of aryllithium and zinc reagents from inexpensive and readily available aryl chlorides by using lithium 4,4′-di-tert-butylbiphenylide (LiDBB) as a lithiation reagent. The resulting organometallic reagents underwent subsequent reactions with a variety of electrophiles, such as an aldehydes, DMF, PhSSO2Ph, TsCN, an aryl halide, or an acid chloride (through Pd-catalyzed cross-coupling). Aryl chlorides bearing substituents, including methoxy, 3,4-methylenedioxy, fluoride, TMS, OTMS, NMe2, acetal, and ketal, were shown to be appropriate substrates. Interestingly, aryl chlorides containing a formyl group could also be used, provided that the formyl group was temporarily converted into an α-amino alkoxide by using the lithium amide of N,N,N′-trimethylethylenediamine (LiTMDA). The presence of a hydroxyl group was also tolerated when it was deprotonated with n-BuLi prior to the addition of LiDBB.
Ligand-Free Copper-Catalyzed Negishi Coupling of Alkyl-, Aryl-, and Alkynylzinc Reagents with Heteroaryl Iodides
Thapa, Surendra,Kafle, Arjun,Gurung, Santosh K.,Montoya, Adam,Riedel, Patrick,Giri, Ramesh
supporting information, p. 8236 - 8240 (2015/07/07)
Reported herein is an unprecedented ligand-free copper-catalyzed cross-coupling of alkyl-, aryl-, and alkynylzinc reagents with heteroaryl iodides. The reaction proceeds at room temperature for the coupling of primary, secondary, and tertiary alkylzinc reagents with heteroaryl iodides without rearrangement. An elevated temperature (100 C) is required for aryl-heteroaryl and alkynyl-heteroaryl couplings.
Catalytic asymmetric synthesis of tertiary alkyl fluorides: Negishi cross-couplings of racemic α,α-dihaloketones
Liang, Yufan,Fu, Gregory C.
supporting information, p. 5520 - 5524 (2014/05/06)
The development of new approaches to the construction of fluorine-containing target molecules is important for a variety of scientific disciplines, including medicinal chemistry. In this Article, we describe a method for the catalytic enantioselective syn
