1609183-44-9Relevant academic research and scientific papers
A unified strategy for iron-catalyzed ortho-alkylation of carboxamides
Fruchey, Erin R.,Monks, Brendan M.,Cook, Silas P.
, p. 13130 - 13133 (2014)
Using 8-aminoquinoline-based aryl carboxamides, the direct ortho-alkylation can be achieved in high yields in the presence of an iron source, 1,2-bis(diphenylphosphino) ethane (dppe) and phenylmagnesium bromide. The reactions proceed without overalkylation and provide high levels of regioselectivity. The benzylation reactions can be performed in air with reagent-grade THF, while the alkylation works well with unactivated secondary bromides and iodides in 2-methyltetrahydrofuran. Moreover, the reactions only require 5 - 10 min.
Facile Synthesis of Alkylidene Phthalides by Rhodium-Catalyzed Domino C?H Acylation/Annulation of Benzamides with Aliphatic Carboxylic Acids
Liu, Sien,He, Bangyue,Li, Hongyi,Zhang, Xiaofeng,Shang, Yaping,Su, Weiping
, p. 15628 - 15633 (2021/10/05)
The Rh-catalyzed ortho-C(sp2)?H functionalization of 8-aminoquinoline-derived benzamides with aliphatic acyl fluorides generated in situ from the corresponding acids has been developed. This reaction initiated with 8-aminoquinoline-directed ortho-C(sp2)?H acylation, which was accompanied by subsequent intramolecular nucleophilic acyl substitution of amide group to produce alkylidene phthalides This approach exhibits high stereo-selectivity for Z-isomer products, and tolerates a variety of functional groups as well as aliphatic carboxylic acids with diverse structural scaffolds.
Pd-catalyzed monoselective ortho -C-H alkylation of N -quinolyl benzamides: Evidence for stereoretentive coupling of secondary alkyl iodides
Zhang, Shu-Yu,Li, Qiong,He, Gang,Nack, William A.,Chen, Gong
, p. 531 - 539 (2015/01/30)
We report a method for the monoselective alkylation of ortho-C-H bonds of N-quinolyl benzamides with both primary and secondary alkyl halides under palladium catalysis. With promotion by NaHCO3 and (BnO)2PO2H or (PhO)
Nickel-catalyzed C-H alkylations: Direct secondary alkylations and trifluoroethylations of arenes
Song, Weifeng,Lackner, Sebastian,Ackermann, Lutz
supporting information, p. 2477 - 2480 (2014/03/21)
A versatile nickel catalyst allowed for C-H alkylations of unactivated arenes with challenging secondary alkyl bromides and chlorides. The high catalytic efficacy also set the stage for direct secondary alkylations of indoles as well as C-H trifluoroethylations with ample substrate scope. In an absence of activation: A robust nickel(II) catalyst enabled secondary alkylations of unactivated aryl C-H bonds with secondary alkyl bromides and chlorides with ample substrate scope. Based on this system the first C-H trifluoroethylations of arenes with unactivated C-H bonds could be carried out (see scheme; Q=8-quinolinyl). Copyright
