91767-34-9Relevant academic research and scientific papers
Copper-Catalyzed Oxidative Benzylic C(sp3)?H Cyclization for the Synthesis of β-Lactams
Nozawa-Kumada, Kanako,Saga, Satoshi,Matsuzawa, Yuta,Hayashi, Masahito,Shigeno, Masanori,Kondo, Yoshinori
supporting information, p. 4496 - 4499 (2020/04/10)
β-Lactams are important structural motifs because of their ubiquity in natural products and pharmaceuticals. We report herein a Cu-catalyzed intramolecular oxidative C(sp3)?H amidation for the synthesis of β-lactams using tBuOOtBu. This method
Nickel-catalyzed direct thiolation of C(sp3)-H bonds in aliphatic amides
Wang, Xie,Qiu, Renhua,Yan, Chunyang,Reddy, Vutukuri Prakash,Zhu, Longzhi,Xu, Xinhua,Yin, Shuang-Feng
supporting information, p. 1970 - 1973 (2015/04/27)
Nickel-catalyzed thiolation of the inactivated methyl C(sp3)-H bonds of aliphatic amides with disulfide is described. It is a novel strategy for the synthesis of thioethers with the ultimate goal of generating thioether carboxylic acids with various functional groups.
Nickel-catalyzed direct thiolation of unactivated C(sp3)-H bonds with disulfides
Yan, Sheng-Yi,Liu, Yue-Jin,Liu, Bin,Liu, Yan-Hua,Zhang, Zhuo-Zhuo,Shi, Bing-Feng
supporting information, p. 7341 - 7344 (2015/04/27)
The first nickel-catalyzed thiolation of unactivated C(sp3)-H bonds with disulfides was described. This transformation uses (dppp)NiCl2 as a catalyst and BINOL as a ligand, which are efficient for the thiolation of β-methyl C(sp
Nickel-catalyzed directed sulfenylation of sp2 and sp3 C-H bonds
Ye, Xiaohan,Petersen, Jeffrey L.,Shi, Xiaodong
supporting information, p. 7863 - 7866 (2015/05/13)
Directed sulfenylation of both sp2 and sp3 C-H bonds was achieved through nickel catalyzed directed C-S bond formation, giving the desired product in good to excellent yield (up to 90%). Other metal cations, including Cu, Fe, Pd, Rh, Ru and Co, gave almost no reaction under identical conditions, which highlighted the unique reactivity of this Ni system.
Palladium(0)/PAr3-catalyzed intermolecular amination of C(sp3)-H bonds: Synthesis of β-amino acids
He, Jian,Shigenari, Toshihiko,Yu, Jin-Quan
supporting information, p. 6545 - 6549 (2015/06/08)
An intermolecular C(sp3)-H amination using a Pd0/PAr3 catalyst was developed. The reaction begins with oxidative addition of R2N-OBz to a Pd0/PAr3 catalyst and subsequent cleavage of a C(sp3)-H bond by the generated Pd-NR2 intermediate. The catalytic cycle proceeds without the need for external oxidants in a similar manner to the extensively studied palladium(0)-catalyzed C-H arylation reactions. The electron-deficient triarylphosphine ligand is crucial for this C(sp3)-H amination reaction to occur.
Nickel-Catalyzed Direct C (sp3)-H Arylation of Aliphatic Amides with Thiophenes
Wang, Xie,Zhu, Longzhi,Chen, Sihai,Xu, Xinhua,Au, Chak-Tong,Qiu, Renhua
supporting information, p. 5228 - 5231 (2015/11/18)
Nickel-catalyzed heteroarylation of the inactive methyl C(sp3)-H bond of aliphatic amide with heteroarenes is described. The method takes advantage of chelation assistance by an 8-aminoquinolinyl moiety. The synthetic reaction has good tolerance toward functional groups, and it can be used in the construction of various kinds of alkyl-substituted heteroarenes.
Nickel-catalyzed direct arylation of C(sp3)-H bonds in aliphatic amides via bidentate-chelation assistance
Aihara, Yoshinori,Chatani, Naoto
supporting information, p. 898 - 901 (2014/02/14)
The Ni-catalyzed, direct arylation of C(sp3)-H (methyl and methylene) bonds in aliphatic amides containing an 8-aminoquinoline moiety as a bidentate directing group with aryl halides is described. Deuterium-labeling experiments indicate that the C-H bond cleavage step is fast and reversible. Various nickel complexes including both Ni(II) and Ni(0) show a high catalytic activity. The results of a series of mechanistic experiments indicate that the catalytic reaction does not proceed through a Ni(0)/Ni(II) catalytic cycle, but probably through a Ni(II)/Ni(IV) catalytic cycle.
Nickel-catalyzed site-selective alkylation of unactivated C(sp 3)-H bonds
Wu, Xuesong,Zhao, Yan,Ge, Haibo
supporting information, p. 1789 - 1792 (2014/03/21)
The direct alkylation of unactivated sp3 C-H bonds of aliphatic amides was achieved via nickel catalysis with the assist of a bidentate directing group. The reaction favors the C-H bonds of methyl groups over the methylene C-H bonds and tolerates various functional groups. Moreover, this reaction shows a predominant preference for sp3 C-H bonds of methyl groups via a five-membered ring intermediate over the sp2 C-H bonds of arenes in the cyclometalation step.
Copper-catalyzed site-selective intramolecular amidation of unactivated C(sp3)-H bonds
Wu, Xuesong,Zhao, Yan,Zhang, Guangwu,Ge, Haibo
supporting information, p. 3706 - 3710 (2014/04/17)
The intramolecular dehydrogenative amidation of aliphatic amides, directed by a bidentate ligand, was developed using a copper-catalyzed sp3 C-H bond functionalization process. The reaction favors predominantly the C-H bonds of β-methyl groups over the unactivated methylene C-H bonds. Moreover, a preference for activating sp3 C-H bonds of β-methyl groups, via a five-membered ring intermediate, over the aromatic sp2 C-H bonds was also observed in the cyclometalation step. Additionally, sp3 C-H bonds of unactivated secondary sp3 C-H bonds could be functionalized by favoring the ring carbon atoms over the linear carbon atoms. Getting ahead on tams: The intramolecular dehydrogenative amidation of aliphatic amides, directed by a bidentate ligand, was developed using a copper-catalyzed sp 3 C-H bond functionalization process to deliver β-lactams. The reaction favors the C-H bonds of β-methyl groups over the unactivated methylene C-H bonds, as well as aromatic C(sp2)-H bonds and unactivated secondary C(sp3)-H bonds of rings.
