28131-24-0Relevant articles and documents
Photochemical regioselective C(sp3)-H amination of amides using N-haloimides
Pan, Lei,Elmasry, Joseph,Osccorima, Tomas,Cooke, Maria Victoria,Laulhé, Sébastien
supporting information, p. 3389 - 3393 (2021/05/07)
A metal-free regioselective C(sp3)-H amination of amides using N-haloimides in the presence of lithium tert-butoxide and visible light is presented herein. This photoexcited approach is straightforward, and it aminates a wide variety of amides under mild conditions without the use of photocatalysts, external radical initiators, or oxidants. A halogen-bonded intermediate between the tert-butoxide base and the N-haloimide is proposed to be responsible for the increased photoreactivity. Calculations show that the formation of this electron donor-acceptor complex presents an exergonic energy profile.
Amide Effects in C?H Activation: Noncovalent Interactions with L-Shaped Ligand for meta Borylation of Aromatic Amides
Bisht, Ranjana,Hoque, Md Emdadul,Chattopadhyay, Buddhadeb
supporting information, p. 15762 - 15766 (2018/11/10)
A new concept for the meta-selective borylation of aromatic amides is described. It has been demonstrated that while esters gave para borylations, amides lead to meta borylations. For achieving high meta selectivity, an L-shaped bifunctional ligand has been employed and engages in an O???K noncovalent interaction with the oxygen atom of the moderately distorted amide carbonyl group. This interaction provides exceptional control for meta C?H activation/borylation.
Nickel-catalyzed C-O bond reduction of aryl and benzyl 2-pyridyl ethers
Li, Jing,Wang, Zhong-Xia
supporting information, p. 2138 - 2141 (2018/03/06)
The reduction of aryl and benzyl 2-pyridyl ethers with sodium isopropoxide was carried out via nickel-catalyzed C-OPy bond cleavage, giving reductive products in reasonable to excellent yields. This method allowed the 2-pyridyloxy group to be directly rem
Nickel-catalyzed C-N bond reduction of aromatic and benzylic quaternary ammonium triflates
Yi, Yuan-Qiu-Qiang,Yang, Wen-Cheng,Zhai, Dan-Dan,Zhang, Xiang-Yu,Li, Shuai-Qi,Guan, Bing-Tao
, p. 10894 - 10897 (2016/09/09)
A nickel-catalyzed, efficient C-N bond reduction of aromatic and benzylic ammonium triflates has been developed using sodium isopropoxide as a reducing agent. The high efficiency, mild conditions, and good compatibility with various substituents made this method an effective supplement to the current catalytic hydrogenation reactions. Combining this reductive deamination reaction with directed aromatic functionalization reactions, a powerful strategy for regioselective functionalization of arenes was demonstrated using dialkylamine groups as traceless directing groups.
Pd(II)/Ag(I)-Promoted One-Pot Synthesis of Cyclic Ureas from (Hetero)Aromatic Amines and Isocyanates
Youn, So Won,Kim, Yi Hyun
supporting information, p. 6140 - 6143 (2016/12/09)
A simple and facile one-pot reaction has been developed to afford a diverse range of N,N′-disubstituted benzimidazolones and imidazopyridinones containing two differently substituted N atoms. A cooperative Pd(II)/Ag(I) system promotes the sequential addition/intramolecular C-H amidation reaction of (hetero)aromatic amines and isocyanates, leading to the formation of two C-N bonds. A mechanism involving radical intermediates generated by single-electron transfer (SET) in the presence of a Ag2CO3 oxidant and Pd(OAc)2 Lewis acid is proposed. This protocol offers an operationally easy, simple, and robust approach with the use of readily available starting materials, good functional group tolerance, and high efficiency.
Efficient N-Boc protection of amines by a reusable heterogeneous solid acid nanocatalyst at room temperature
Veisi, Hojat,Sedrpoushan, Alireza,Ghazizadeh, Habibollah,Hemmati, Saba
, p. 1451 - 1461 (2016/04/26)
An efficient and rapid protocol for chemoselective N-Boc protection of various structurally different aryl, aliphatic, and heterocyclic amines is reported with (Boc)2O using mesoporous silica phenylsulfonic acid (SBA-15-Ph-SO3H) as a recyclable and heterogeneous solid acid nanocatalyst under solvent-free condition at ambient temperature. The catalyst can be easily recovered and reused for ten reaction cycles for protection of amines without considerable loss of activity. The advantages of this green method are simplicity, easy workup, chemoselectivity, short reaction time, and excellent yield.
Palladium-catalyzed oxidative carbonylation of aromatic C-H bonds of N -alkylanilines with CO and alcohols for the synthesis of o -aminobenzoates
Chen, Ming,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui
, p. 1258 - 1263 (2015/01/30)
A Pd(II)-catalyzed C-H monocarbonylation of N-alkylanilines for the synthesis of o-aminobenzoates has been developed. Various aliphatic alcohols and phenol were tolerated in the reaction to afford the corresponding o-aminobenzoates in good yields under mild balloon pressure of CO.
Copper-catalyzed intermolecular C(sp3)-H bond functionalization towards the synthesis of tertiary carbamates
Chikkade, Prasanna Kumara,Kuninobu, Yoichiro,Kanai, Motomu
, p. 3195 - 3200 (2015/06/17)
We describe the development of an intermolecular unactivated C(sp3)-H bond functionalization towards the direct synthesis of tertiary carbamates. The transformation proceeded using a readily available, abundant first-row transition metal catalyst (copper), and isocyanates as the source of the amide moiety. This is a novel strategy for direct transformation of a variety of unactivated hydrocarbon feedstocks to N-alkyl-N-aryl and N,N-dialkyl carbamates without pre-functionalization or installation of a directing group. The reaction had a broad substrate scope with 3° > 2° > 1° site selectivity. The reaction proceeded even on a gram scale, and a corresponding free amine was directly obtained when the reaction was performed at high temperature. Kinetic studies suggested that radical-mediated C(sp3)-H bond cleavage was the rate-determining step.
A 2,6-bis(phenylamino)pyridinato titanium catalyst for the highly regioselective hydroaminoalkylation of styrenes and 1,3-butadienes
Doerfler, Jaika,Preuss, Till,Schischko, Alexandra,Schmidtmann, Marc,Doye, Sven
supporting information, p. 7918 - 7922 (2014/08/05)
The C-C bond forming catalytic hydroaminoalkylation of terminal alkenes, 1,3-dienes, or styrenes allows a direct and highly atom efficient (100 %) synthesis of amines which can result in the formation of two regioisomers, the linear and the branched product. We present a new titanium catalyst with 2,6-bis(phenylamino)pyridinato ligands for intermolecular hydroaminoalkylation reactions of styrenes and 1-phenyl-1,3-butadienes that delivers the corresponding linear hydroaminoalkylation products with excellent regioselectivities. Linear progress: A new Ti complex with 2,6-bis(phenylamino) pyridinato ligands catalyzes highly regioselective hydroaminoalkylation reactions of styrenes. The process that directly gives access to the corresponding linear hydroaminoalkylation products offers a new and flexible synthetic approach towards pharmaceutically important 3-arylpropylamines. It is also possible to convert (E)-1-phenyl-1,3-butadienes into the corresponding linear products.
A mild and green method for the N-BOC protection of amines without assistant of catalyst under solvent-free conditions
Mojtahedi, Mohammad Majid,Niknejad, Nina,Veisi, Hojat
, p. 121 - 125 (2013/07/26)
A facile, green and versatile method for the Boc protection of amines has been developed by a treatment with (Boc)2O without any additive at room temperature. The method is general for the preparation of N-Boc derivatives of aliphatic (acyclic and cyclic), aromatic, and heteroaromatic amines; primary and secondary amines. The advantages of this method are green, simplicity, short reaction times and excellent yields.
