141978-49-6Relevant academic research and scientific papers
Enantioselective Copper-Catalyzed Alkylation of Quinoline N-Oxides with Vinylarenes
Yu, Songjie,Sang, Hui Leng,Ge, Shaozhong
, p. 15896 - 15900 (2017)
An asymmetric copper-catalyzed alkylation of quinoline N-oxides with chiral Cu–alkyl species, generated by migratory insertion of a vinylarene into a chiral Cu?H complex, is reported. A variety of quinoline N-oxides and vinylarenes underwent this Cu-catalyzed enantioselective alkylation reaction, affording the corresponding chiral alkylated N-heteroarenes in high yield with high-to-excellent enantioselectivity. This enantioselective protocol represents the first general and practical approach to access a wide range of chiral alkylated quinolines.
Aerobic cross-dehydrogenative couplings of N-heteroarenes with toluene derivatives at room temperature
Chen, Yufeng,Deng, Guo-Jun,Huang, Huawen,Sun, Zhaozhao,Wang, Qiao-Lin
supporting information, p. 7790 - 7795 (2021/10/12)
A set of mild aerobic cross-dehydrogenative couplings of N-heteroarenes with the benzylic C(sp3)-H bond has been achieved by using visible-light-induced photocatalysis. This approach was found to provide a sustainable alternative to Minisci benzylation reactions using readily accessible toluene derivatives as benzylating agents. The unique combination of photocatalysis, bromo radical mediation, and aerobic oxidation proved to be the key for the success of the transformation. Mechanistic studies revealed the feasibility of both oxidative and reductive quenching of the excited photocatalyst in the initial step.
Pd-PEPPSI-IPent-SiO2: A Supported Catalyst for Challenging Negishi Coupling Reactions in Flow
Price, Gregory A.,Hassan, Abbas,Chandrasoma, Nalin,Bogdan, Andrew R.,Djuric, Stevan W.,Organ, Michael G.
supporting information, p. 13347 - 13350 (2017/10/17)
A silica-supported precatalyst, Pd-PEPPSI-IPent-SiO2, has been prepared and evaluated for its proficiency in the Negishi cross-coupling of hindered and electronically deactivated coupling partners. The precatalyst Pd-PEPPSI-IPent loaded onto packed bed columns shows high catalytic activity for the room-temperature coupling of deactivated/hindered biaryl partners. Also for the first time, the flowed Csp3–Csp2 coupling of secondary alkylzinc reagents to (hetero)aromatics has been achieved with high selectivity with Pd-PEPPSI-IPent-SiO2. These couplings required residence times as short as 3 minutes to effect completion of these challenging transformations with excellent selectivity for the nonrearranged product.
Reactivity of benzyl radicals: The trapping of primary, secondary and tertiary benzyl radicals with heterocyclic bases
Brivio, Luigi,Caronna, Tullio,Fontana, Francesca,Gambarotti, Cristian,Mele, Andrea,Sora, Isabella Natali,Punta, Carlo,Recupero, Francesco
experimental part, p. 112 - 114 (2010/12/18)
A photochemical benzylation of protonated quinolines was realized by single electron transfer (SET) to the excited state of the quinoline from the aromatic reactant. The benzylated product is formed by cross-coupling between the benzyl radical and the heterocyclic radical when they are in close proximity to one another. This allows the formation of products which are, to the best of our knowledge, unaccessible in other ways and which have now been obtained for the first time.
