1088187-91-0Relevant articles and documents
Copper-Mediated ortho-Arylation of Benzamides with Arylboronic Acid
Gui, Qingwen,Chen, Xiang,Hu, Liang,Wang, Dadian,Liu, Jidan,Tan, Ze
, p. 509 - 514 (2016)
The copper-mediated direct ortho C-H bond arylation of benzamide derivatives with arylboronic acids was achieved by employing an 8-aminoquinoline moiety as the bidentate directing group. Various biaryls were synthesized in good yields with excellent regioselectivity. The reaction shows good functional group compatibility and proceeds in a highly selective manner at the ortho-position of the benzamides. Deuterium-labelling experiments indicated that the ortho C-H bond cleavage of benzamide was involved in the rate-determining step of the arylation.
Cobalt-promoted selective arylation of benzamides and acrylamides with arylboronic acids
Hu, Liang,Gui, Qingwen,Chen, Xiang,Tan, Ze,Zhu, Gangguo
, p. 11070 - 11075 (2016)
A novel cobalt-promoted arylation of aryl C-H bonds with arylboronic acids has been realized by using 8-aminoquinoline as the directing group. The reaction tolerated a wide variety of functional groups and diversely substituted ortho-arylated benzamides were efficiently synthesized in good to excellent yields. Even though a catalytic amount of a Co-salt was enough to effect the transformation, better yields were obtained with a stoichiometric amount of the Co-salt. A notable feature of this newly developed protocol is that acrylamides, which cannot be arylated using copper salts as the promoter, can also be efficiently arylated. In addition, the stereochemistry of these arylation products can be largely retained under the standard conditions.
Iron-catalyzed ortho -allylation of aromatic carboxamides with allyl ethers
Asako, Sobi,Ilies, Laurean,Nakamura, Eiichi
, p. 17755 - 17757 (2013)
Arenes possessing an N-(quinolin-8-yl)amide directing group are ortho-allylated with allyl phenyl ether in the presence of an iron/diphosphine catalyst and an organometallic base at 50-70 C. The reaction proceeds via fast iron-catalyzed C-H activation, fo
Aryne Multicomponent Reactions by Directed C?H Activation
Sunnam, Sunil Kumar,Belani, Jitendra D.
, p. 8846 - 8850 (2021/05/31)
Arylation via ortho C?H activation by the aid of directing groups has been explored recently by many researchers. Herein, a palladium-catalyzed C?H arylation using 8-aminoquinoline as a bidentate directing group has been developed. The reaction furnishes only C?H arylation, unlike previous methods where cyclization to corresponding isoquinolones is observed. More interestingly, sequential C?H functionalization was observed when methylacrylate and acrylonitrile was added; this led to C?H olefination with the aryl group, which was installed from the aryne precursor.
Rhodium-Catalyzed Alkylation of C?H Bonds in Aromatic Amides with Non-activated 1-Alkenes: The Possible Generation of Carbene Intermediates from Alkenes
Yamaguchi, Takuma,Natsui, Satoko,Shibata, Kaname,Yamazaki, Ken,Rej, Supriya,Ano, Yusuke,Chatani, Naoto
, p. 6915 - 6919 (2019/05/10)
The alkylation of C?H bonds (hydroarylation) in aromatic amides with non-activated 1-alkenes using a rhodium catalyst and assisted by an 8-aminoquinoline directing group is reported. The addition of a carboxylic acid is crucial for the success of this reaction. The results of deuterium-labeling experiments indicate that one of deuterium atoms in the alkene is missing, suggesting that the reaction does not proceed through the commonly accepted mechanism for C?H alkylation reactions. Instead the reaction is proposed to proceed through a carbene mechanism. The carbene mechanism is also supported by preliminary DFT calculations.
