57144-65-7Relevant academic research and scientific papers
Rapid Construction of Tetralin, Chromane, and Indane Motifs via Cyclative C-H/C-H Coupling: Four-Step Total Synthesis of (±)-Russujaponol F
Zhuang, Zhe,Herron, Alastair N.,Liu, Shuang,Yu, Jin-Quan
supporting information, p. 687 - 692 (2021/01/25)
The development of practical C-H/C-H coupling reactions remains a challenging yet appealing synthetic venture because it circumvents the need to prefunctionalize both coupling partners for the generation of C-C bonds. Herein we report a cyclative C(sp3)-H/C(sp2)-H coupling reaction of free aliphatic acids enabled by a cyclopentane-based mono-N-protected β-amino acid ligand. This reaction uses inexpensive sodium percarbonate (Na2CO3·1.5H2O2) as the sole oxidant and generates water as the only byproduct. A range of biologically important scaffolds, including tetralins, chromanes, and indanes, can be easily prepared by this protocol. Finally, the synthetic application of this methodology is demonstrated by the concise total synthesis of (±)-russujaponol F in a four-step sequence starting from readily available phenylacetic acid and pivalic acid through sequential functionalizations of four C-H bonds.
Auxiliary-Directed C(sp3)?H Arylation by Synergistic Photoredox and Palladium Catalysis
Czyz, Milena L.,Lupton, David W.,Polyzos, Anastasios
, p. 14450 - 14453 (2017/10/07)
Herein we describe the auxiliary-directed arylation of unactivated C(sp3)?H bonds with aryldiazonium salts, which proceeds under synergistic photoredox and palladium catalysis. The site-selective arylation of aliphatic amides with α-quaternary centres is achieved with high selectivity for β-methyl C(sp3)?H bonds. This operationally simple method is compatible with carbocyclic amides, a range of aryldiazonium salts and proceeds at ambient conditions.
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.
Nickel-catalyzed site-selective alkylation of unactivated C(sp 3)-H bonds
Wu, Xuesong,Zhao, Yan,Ge, Haibo
, 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
, 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.
Nickel-catalyzed direct arylation of C(sp3)-H bonds in aliphatic amides via bidentate-chelation assistance
Aihara, Yoshinori,Chatani, Naoto
, 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.
Palladium-catalyzed methylation and arylation of sp2 and sp 3 C-H bonds in simple carboxylic acids
Giri, Ramesh,Maugel, Nathan,Li, Jiao-Jie,Wang, Dong-Hui,Breazzano, Steven P.,Saunders, Lindsey B.,Yu, Jin-Quan
, p. 3510 - 3511 (2007/10/03)
The use of preformed sodium carboxylates as substrates led to the first observation of facile Pd-insertions into sp3 β-C-H bonds in simple aliphatic acids. Consequently, Pd-catalyzed methylation and arylation of o-C-H bonds in benzoic acids and β-C-H bonds in aliphatic acids using either a phenylboronate, methylboronic acid, or ArI have been achieved via a C-H activation/C-C coupling sequence. Copyright
Indaneacetic acid derivatives
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, (2008/06/13)
This invention provides new compounds of formula I, STR1 wherein R1 is lower alkyl, R2 is hydrogen or lower alkyl, R3 is hydrogen or lower alkyl, R4 is hydrogen or lower alkyl, R5 is hydrogen, chlorine or lower alkyl, and each of R6 and R7 is hydrogen, or, when R5 is hydrogen, R6 may also be chlorine or lower alkyl, and R7 chlorine or lower alkyl, Useful as anti-phlogistic and anti-arthritic agents.
