Using Han Hao, Kyle A. Thompson, Zachary M. Hudson, Laurel L. Schafer. These reactions of fundamental simplicity represent the most atom efficient processes for the formation of amines, enamines and imines, which are important bulk and fine chemicals or building blocks in organic synthesis. Bond Addition to Alkynes and Heterocumulenes. Guangqiang Xu, Li Zhou, Chengdong Lv, Mo Xian, Qinggang Wang. You do not have JavaScript enabled. Chaofan Huang, Hui Qian, Wanli Zhang, Shengming Ma. Many enamines are found in many natural and synthetic compounds possessing interesting physiological and biological activities. * However, in contrast to metal-catalyzed hydroamination, the base-mediated hydroamination of alkynes has not been extensively studied. HN Copper-catalyzed stereo- and chemoselective synthesis of enaminones via Michael type addition. The direct addition of ammonia or primary and secondary amines to non-activated alkenes and alkynes is potentially the most efficient approach towards the synthesis of higher substituted nitrogen-containing products. ]benzimidazoles from 2-Alkynyl-3,3-Difluoro-3 Huamin Wang, Yongli Li, Zilu Tang, Shengchun Wang, Heng Zhang, Hengjiang Cong. XX is the XXth reference in the list of references. hydrogen. Chemo-, Regio-, and Stereoselective N-Alkenylation of Pyrazoles/Benzpyrazoles Using Activated and Unactivated Alkynes. Inorganic base-mediated stereoselective hydroamination of arylalkynes with imidazole: An efficient access to N -vinylimidazoles. A DFT Study on CuH-Catalyzed Reductive Relay Hydroamination for Synthesis of Remote-Chiral Amine. the whole article in a third party publication with the exception of reproduction Acetylenes in the Superbase-Promoted Assembly of Carbocycles and Heterocycles. If you are the author of this article you still need to obtain permission to reproduce Fei Ling, Lian Xiao, Lu Fang, Cong Feng, Zhen Xie, Yaping Lv, Weihui Zhong. You have to login with your ACS ID befor you can login with your Mendeley account. Mechanistic insights into Pd(0)-catalyzed intermolecular and intramolecular hydroamination of methylenecyclopropanes: a computational study. Justin M. Salvant, Anne V. Edwards, Daniel Z. Kurek, and Ryan E. Looper . Holmes, Amy J. Ruddlesden, Simon B. Duckett. Pengqing Ye, Yinlin Shao, Leping Xie, Keting Shen, Tianxing Cheng, Jiuxi Chen. Jiao Long, Peng Wang, Wang Wang, Yuqiang Li, Guoyin Yin. Iron(II)-Catalyzed Hydroamination of Isocyanates. Palladium-Catalyzed Aerobic Oxidative Hydroamination of Vinylarenes Using Anilines: A Wacker-Type Amination Pathway. Rahul P., Nitha P. R., Vishnu K. Omanakuttan, Sheba Ann Babu, P. Sasikumar, Vakayil K. Praveen, Henning Hopf, Jubi John. Interestingly, the stereoselectivity of the addition products (kinetically stable Z and thermodynamically stable E isomers) was found to be dependent upon time. The development of synthetic protocols for such molecules and their transformation is a persistent research topic in pharmaceutical and organic chemistry. Synthesis and catalytic activity in reductive amination using carbon monoxide as a reducing agent. -Indoles. 9-11, D-26111 Oldenburg, Germany Carmen Nájera, Irina P. Beletskaya, Miguel Yus. Computational and experimental investigation on the BCl Corresponding authors, a DBU-Catalyzed Alkyne–Imidate Cyclization toward 1-Alkoxypyrazino[1,2-a]indole Synthesis. 9-11, D-26111 Oldenburg, Germany, Instructions for using Copyright Clearance Center page. or in a thesis or dissertation provided that the correct acknowledgement is given Hydroamination is conspicuously superior to the other accessible methods, such as the imination of ketones or the aminomercuration/demercuration of alkynes, that involve the stoichiometric use of toxic reagents. Photochemical Generation of Nitrogen-Centered Amidyl, Hydrazonyl, and Imidyl Radicals: Methodology Developments and Catalytic Applications. Simple ZnEt This method represents an attractive strategy for the construction of a broad range of nitrogen-containing compounds that prevents the formation of byproducts in the creation of a C–N linkage. Biosynthesis of Biscognienyne B Involving a Cytochrome P450‐Dependent Alkynylation. Hongyu Wang, Yanfei Ren, Kaiye Wang, Yunquan Man, Yanan Xiang, Na Li, Bo Tang. A Simple Protocol for the Stereoselective Construction of Enaminyl Sulfonyl Fluorides. In this Account, we summarize our latest achievements in regio-, stereo-, and chemoselective hydroamination chemistry of N-nucleophiles with alkynes using a superbasic medium to produce a broad range of highly functionalized vinyl and styryl enamines, which are valuable and versatile synthetic intermediates for the synthesis of bioactive compounds. The presence of a base is thought to facilitate the attack of nitrogen nucleophiles, such as indoles, pyrroles, and imidazoles, on unsaturated carbon substrates through the activation of the triple bond and thus transforming the electron-rich alkyne into an electrophile. Intramolecular Hydroamination of Alkenes. Consequently, the development of corresponding hydroamination reactions has received much attention and great progress has been achieved in the case of catalytic hydroaminations of alkynes over the past four years. However, if it is necessary for the discussion, older results and intramolecular reactions, which can be achieved more easily, will be mentioned as well. as a catalyst in carbodiimide hydroalkynylation: structural and mechanistic studies. Hydroamination of isocyanates and isothiocyanates by alkaline earth metal initiators supported by a bulky iminopyrrolyl ligand. CuH-catalysed hydroamination of arylalkynes with hydroxylamine esters – a computational scrutiny of rival mechanistic pathways. Synthesis of 1,2-Fused Tricyclic Indoles via Cu-/Base-Mediated Hydroamination of Alkynes. Among the plethora of C–N bond-forming reactions available in the arsenal of organic chemists, the hydroamination of alkynes is a very useful process, which is generally performed under metal catalysis. These metrics are regularly updated to reflect usage leading up to the last few days. hydrogen to hyperpolarize amines, amides, carboxylic acids, alcohols, phosphates, and carbonates. * Stephan Metal- and acid-free, TBN-mediated direct C H nitration of arenes. Fax: +49-(0)511-762-3011. Kapil Mohan Saini, Rakesh K. Saunthwal, Sushmita, Akhilesh K. Verma. ) Synthesis of Imidazolidin-2-ones and Imidazol-2-ones via Base-Catalyzed Intramolecular Hydroamidation of Propargylic Ureas under Ambient Conditions. Alexey 3 Direct and indirect hyperpolarisation of amines using Christine Reproduced material should be attributed as follows: If the material has been adapted instead of reproduced from the original RSC publication article provided that the correct acknowledgement is given with the reproduced material. Get article recommendations from ACS based on references in your Mendeley library. contained in this article in third party publications ‐Formyl Phenylacetylenes with Secondary Amines: Access to 1,3‐Diamino‐1 Anti‐Markovnikov Hydroamination of Racemic Allylic Alcohols to Access Chiral γ‐Amino Alcohols. para It is worthwhile to note that hydroaminated products formed by the addition reaction can further be utilized for the synthesis of indolo-/pyrrolo[2,1-a]isoquinolines, naphthyridines, and bisindolo/pyrrolo[2,1-a]isoquinolinesvia tandem cyclization. Light-Driven, Zirconium-Catalyzed Hydrophosphination with Primary Phosphines. L. A. Grishchenko, L. N. Parshina, V. V. Kireeva, B. of the whole article in a thesis or dissertation. If you are the author of this article you still need to obtain permission to reproduce Catalytic additions of ammonia or primary and secondary amines to non-activated alkenes and alkynes are called hydroaminations.