- Palladium(ii)-catalysed ortho-arylation of N-benzylpiperidines
-
PdII-catalysed ortho-arylation of benzylic heterocycles with arylboronic acid pinacol esters (Ar-BPin) via directed C-H bond activation to generate the desired biaryl products is reported. This methodology is efficient and applicable to a wide range of functionalised Ar-BPin and benzylic heterocycles, allowing the direct synthesis of important biaryl motifs in modest to good yield. This journal is
- Tan, Peng Wen,Haughey, Maxwell,Dixon, Darren J.
-
-
Read Online
- N?N Bond Formation Using an Iodonitrene as an Umpolung of Ammonia: Straightforward and Chemoselective Synthesis of Hydrazinium Salts
-
The formation of hydrazinium salts by N?N bond formation has typically involved the use of hazardous and difficult to handle reagents. Here, mild and operationally simple conditions for the synthesis of hydrazinium salts are reported. Electrophilic nitrogen transfer to the nitrogen atom of tertiary amines is achieved using iodosylbenzene as oxidant and ammonium carbamate as the N-source. The resulting process is highly chemoselective and tolerant to other functional groups. A wide scope is reported, including examples with bioactive molecules. Insights on the structure of hydrazinium salts were provided by X-ray analysis. (Figure presented.).
- Tota, Arianna,Colella, Marco,Carlucci, Claudia,Aramini, Andrea,Clarkson, Guy,Degennaro, Leonardo,Bull, James A.,Luisi, Renzo
-
supporting information
p. 194 - 199
(2020/10/28)
-
- Method for synthesizing Roxatidine intermediate 3-(1-piperidinyl methyl) phenol
-
The invention discloses a method for synthesizing Roxatidine intermediate 3-(1-piperidinyl methyl) phenol and relates to the technical field of organic synthesis. M-anisyl alcohol which is cheap and easy to obtain is used as a raw material and firstly reacts with sulfinyl chloride to produce m-methoxybenzyl chloride, then the m-methoxybenzyl chloride reacts with piperidine to produce 3-(1-piperidinyl methyl) anisole, and finally demethoxylation is performed in hydrobromic acid to obtain the target product 3-(1-piperidinyl methyl) phenol. The route is clear, the yield is high, the amount of produced waste water, gas and residues is small, the recycling of solvent can be realized, the preparation cost is reduced and the cost is less than half of the cost of the original route.
- -
-
-
- Mild and selective Et2Zn-catalyzed reduction of tertiary amides under Hydrosilylation conditions
-
Diethylzinc (Et2Zn) can be used as an efficient and chemoselective catalyst for the reduction of tertiary amides under mild reaction conditions employing cost-effective polymeric silane (PMHS) as the hydride source. Crucial for the catalytic activity was the addition of a substoichiometric amount of lithium chloride to the reaction mixture. A series of amides containing different additional functional groups were reduced to their corresponding amines, and the products were isolated in good-to-excellent yields.
- Kovalenko, Oleksandr O.,Volkov, Alexey,Adolfsson, Hans
-
supporting information
p. 446 - 449
(2015/03/05)
-
- Base-promoted N-alkylation using formamides as the N-sources in neat water
-
An efficient catalyst-free, alternative method for the C-N bond formation reaction of alkyl electrophiles using formamides as the N-sources was achieved under mild conditions. The reaction possesses the advantages of a broad range of substrates scope and wide functional group tolerance. It should also be noted that this process was performed using the environmentally benign water as the sole solvent, and high yield can also be achieved in ten-gram scale.
- Chen, Wen-Xin,Zhang, Cai-Yun,Shao, Li-Xiong
-
p. 880 - 885
(2014/01/23)
-
- Triol-promoted activation of C-F bonds: Amination of benzylic fluorides under highly concentrated conditions mediated by 1,1,1-tris(hydroxymethyl) propane
-
Activation of the C-F bond of benzylic fluorides was achieved using 1,1,1-tris(hydroxymethyl)propane (2) as a hydrogen bonddonating agent. Investigations demonstrated that hydrogen bond-donating solvents are promoting the activation and hydrogen bondaccepting ones are hindering it. However, the reaction is best run under highly concentrated conditions, where solvents cannot interfere with the interaction between the organofluorine compound and the triol. Various benzylic fluorides react with secondary amines or anilines to form benzylic amines in good yields.
- Champagne, Pier Alexandre,Saint-Martin, Alexandre,Drouin, Melina,Paquin, Jean-Francois
-
supporting information
p. 2451 - 2456
(2014/01/06)
-
- NEW BENZOYL UREA DERIVATIVES
-
The new benzoyl urea derivatives of formula (I) wherein the meaning of X and Y independently are hydrogen atom, hydroxy, benzyloxy, amino, nitro, C1-C4 alkylsulfonamido optionally substituted with a halogen atom or halogen atoms, Cs
- -
-
Page/Page column 24
(2008/06/13)
-
- Formic Acid Reduction. XXVIII. Kinetic Studies on the Formic Acid Reduction of 1,1'-Benzylidenedipiperidine
-
The formic acid reduction of 1,1'-benzylidenedipiperidine (1) was kinetically investigated by the carbon dioxide trapping method.Rate data gave the rate equation, v=kobs.The initial mono- and diprotonation of 1 occur in equilibrium, and monoprotonated form is proposed to be an intermediate for the reduction to 1-benzylpiperidine.The isotope effect value (2.69) and the negative ρ substituent effect (similar to that of the formic acid reduction of N-benzylideneaniline) suggest that the reduction of 1 involves the same intermediate step of decarboxylation of the formic acid ester of the α-amino alcohol.
- Fukawa, Hidemichi,Suzuki, Kunio,Sekiya, Minoru
-
p. 2868 - 2873
(2007/10/02)
-