313367-17-8Relevant articles and documents
Sodium Butylated Hydroxytoluene (NaBHT) as a New and Efficient Hydride Source for Pd-Catalysed Reduction Reactions
Sharif, Sepideh,Rodriguez, Michael J.,Lu, Yu,Kopach, Michael E.,Mitchell, David,Hunter, Howard N.,Organ, Michael G.
, p. 13099 - 13103 (2019/10/28)
NaBHT (sodium butylated hydroxytoluene), a hindered and soluble base for the efficient arylation of various base-sensitive amines and (hetero)aryl halides has been found to have an unanticipated role as a hydride donor to reduce (hetero)aryl halides and allylic acetates. Mechanistic studies have uncovered that NaBHT, but not BHT, can deliver multiple hydrides through oxidation of the benzylic methyl group in NaBHT to the aldehyde. Further, performing the reduction with NaBHT-d20 has revealed that the redox-active benzylic position is not the only hydride donor site from NaBHT with one hydride in three coming, presumably, from the tert-butyl groups. The reduction works well under mild conditions and, incredibly, only consumes 20 percent of the NaBHT in the process; the remaining 80 percent can be readily recovered in pure form and reused. This, combined with the low cost of the material in ton-scale quantity, makes it practical and attractive for wider use in industry at scale.
An efficient, one-pot transamidation of 8-aminoquinoline amides activated by tertiary-butyloxycarbonyl
Wu, Wengang,Yi, Jun,Xu, Huipeng,Li, Shuangjun,Yuan, Rongxin
, (2019/04/05)
The efficient, one-pot access to the transamidation of 8-aminoquinoline (8-AQ), notorious for its harsh removal conditions, has been widely employed as an auxiliary in C–H functionalization reactions due to its strong directing ability. In this study, the facile and mild Boc protection of the corresponding 8-AQ amide was critical to activate the amide C(acyl)–N bond by twisting its geometry to lower the amidic resonance energy. Both aryl and alkyl amines proceeded transamidation in one-pot, user-friendly conditions with excellent yields.
Computational Mechanistic Study on the Nickel-Catalyzed C-H/N-H Oxidative Annulation of Aromatic Amides with Alkynes: The Role of the Nickel (0) Ate Complex
Yamazaki, Ken,Obata, Atsushi,Sasagawa, Akane,Ano, Yusuke,Chatani, Naoto
supporting information, p. 248 - 255 (2019/02/01)
Density functional theory (DFT) was used to unveil intimate mechanistic insights on the monodentate-chelation system that is used in the Ni-catalyzed C-H/N-H oxidative annulation of aromatic amides with alkynes, a reaction that was originally reported by
Nickel-Catalyzed Denitrogenative Cross-Coupling Reaction of 1,2,3-Benzotriazin-4(3 H)-ones with Organoboronic Acids: An Easy Access to Ortho-Arylated and Alkenylated Benzamides
Hari Balakrishnan, Madasamy,Sathriyan, Kotturaja,Mannathan, Subramaniyan
supporting information, p. 3815 - 3818 (2018/07/25)
A novel nickel-catalyzed approach to synthesize ortho-arylated and alkenylated benzamides in good to high yields via a denitrogenative cross-coupling reaction of 1,2,3-benzotriazin-4(3H)-ones with organoboronic acids is described. The reaction proceeds th
Amide Boc de-protection method
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Paragraph 0035; 0105; 0106; 0107, (2018/09/13)
The invention discloses an amide Boc de-protection method. The amide Boc de-protection method includes carrying out reaction on Boc protected amide III and amine IV under the condition of the presenceof palladium catalysts to generate new amide V. 8-aminoquinoline can be used as a guide group to be applied to chemical reaction, a process for synthesizing the new amide by means of de-protection isprovided, protecting groups can be easily removed by means of palladium catalysis, the new amide can be generated, and the reaction is high in efficiency. The amide Boc de-protection method has the advantages of environmental friendliness, recyclability and the like.
Cross-Coupling of Primary Amides to Aryl and Heteroaryl Partners Using (DiMeIHeptCl)Pd Promoted by Trialkylboranes or B(C6F5)3
Sharif, Sepideh,Day, Jonathan,Hunter, Howard N.,Lu, Yu,Mitchell, David,Rodriguez, Michael J.,Organ, Michael G.
supporting information, p. 18436 - 18439 (2018/01/08)
Boron-derived Lewis acids have been shown to effectively promote the coupling of amide nucleophiles to a wide variety of oxidative addition partners using Pd-NHC catalysts. Through a combination of NMR spectroscopy and control studies with and without oxygen and radical scavengers, we propose that boron-imidates form under the basic reaction conditions that aid coordination of nitrogen to Pd(II), which is rate limiting, and directly delivers the intermediate for reductive elimination.
Exploiting the Reactivity of Isocyanide: Coupling Reaction between Isocyanide and Toluene Derivatives Using the Isocyano Group as an N1 Synthon
Liu, Zhiqiang,Zhang, Xinglu,Li, Jian,Li, Jianxiong,Li, Feng,Li, Chunju,Jia, Xueshun
, p. 4052 - 4055 (2016/08/30)
An unusual oxidative coupling reaction of isocyanide and toluene derivatives using tetrabutylammonium iodide (TBAI) as a catalyst is disclosed. The experimental results and mechanistic study show that the isocyano group acts formally as an N1 synthon during the transformation, thus expanding the reactivity profile of isocyanide.
Stable and Reusable Binaphthyl-Supported Palladium Catalyst for Aminocarbonylation of Aryl Iodides
Sharma, Nidhi,Sekar, Govindasamy
supporting information, p. 314 - 320 (2016/02/14)
A binaphthyl-supported Pd nanoparticles (Pd-BNP)-catalyzed aminocarbonylation of aryl iodides in the presence of carbon monoxide and amines for the synthesis of amides has been developed. This methodology provides an efficient route for the synthesis of a COX-2 enzyme inhibitor having anti-inflammatory activity.
Synthesis of polysubstituted-1,2,4-triazoles
Liu, Guiyan,Wu, Xueli,Shi, Xuefang
, p. E39-E42 (2013/06/05)
A new series of substituted 1,2,4-triazole derivatives have been synthesized using substituted imido derivatives and isonicotinyl hydrazine (or 4-nitrobenzoylhydrazine) as the key intermediates. These compounds include different donor or acceptor substitu
Efficient manganese/copper bimetallic catalyst for N-arylation of amides and sulfonamides under mild conditions in water
Teo, Yong-Chua,Yong, Fui-Fong,Ithnin, Idzham Khalid,Yio, Siew-Hui Trionna,Lin, Zhiyin
supporting information, p. 515 - 524 (2013/02/26)
An efficient and mild method using a bimetallic MnF2/CuI catalyst at 60 °C in water was developed for the N-arylation of amides and sulfonamides with aryl halides. A variety of functionalized amides and sulfonamides were coupled with different substituted aryl halides to afford the corresponding N-arylated products in good to excellent yields (up to 97 %). An efficient method using a bimetallic MnF2/CuI catalyst in combination with trans-1,2-diaminocyclohexane as the ligand has been developed for the cross-coupling of benzamides and sulfonamides with differently substituted aryl iodides in water. The corresponding N-arylated products were obtained in good to excellent yields (up to 97 %) under the catalytic conditions. Copyright
