Article
Chemistry, Organic
Mengna Liu, Benqiang Cui, Chuntao Zhong, Yanhui Shi, Yanfeng Dang, Changsheng Cao
Summary: A palladium-catalyzed cyanation of aryl dimethylsulfonium salts using K-4[Fe-(CN)(6)]center dot 3H(2)O as the cyanating reagent was successfully developed. The reaction proceeded under base-free conditions and yielded aryl nitriles with up to 92% yields. The protocol also allowed direct transformation of aryl sulfides to aryl nitriles, and the reaction mechanism was investigated using density functional theory calculations.
Article
Chemistry, Organic
Sha Peng, Luo Yang
Summary: A practical and convenient copper-catalyzed method for cyanation of aryl iodides using formamide as the cyano source has been developed. This method offers high yields of various aryl nitriles, and its lower reaction temperature and excellent substrate compatibility make it more attractive in synthetic and pharmaceutical chemistry.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Ruchita R. Thakore, Balaram S. Takale, Vani Singhania, Fabrice Gallou, Bruce H. Lipshutz
Summary: The new technology enables efficient cyanation reactions of highly complex molecules in water, with significant implications for advancing drug synthesis and discovery.
Article
Chemistry, Multidisciplinary
Ying Chen, Lanting Xu, Yongwen Jiang, Dawei Ma
Summary: The combination of copper salts and oxalic diamides enables the synthesis of α-(hetero)aryl nitriles via one-pot decarboxylation under mild conditions. The method demonstrates a broad substrate scope and compatibility with various functionalities and heteroaryls.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Tristan Delcaillau, Philip Boehm, Bill Morandi
Summary: A new functional group metathesis reaction between aryl nitrites and aryl thioethers has been described, utilizing a catalytic system of nickel/dcype to achieve fully reversible transformation in good to excellent yields. This cyanide- and thiol-free reaction demonstrates high functional group tolerance and efficiency for late-stage derivatization of commercial molecules, with synthetic applications showcasing its versatility and utility in multistep synthesis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Review
Chemistry, Applied
Puthukudichola Krishna Soumya, Thottuvazhiyil Balakrishnan Vaishak, Salim Saranya, Gopinathan Anilkumar
Summary: Cyanation reactions play a dominant role in organic synthesis due to the easy conversion of cyanide groups to various other functionalities. Transition metal-catalyzed reactions, particularly rhodium-catalyzed reactions, have attracted attention from organic chemists, leading to the synthesis of highly functionalized products through various cyanation procedures.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yonggang Yan, Jinjin Sun, Gang Li, Liu Yang, Wei Zhang, Rui Cao, Chao Wang, Jianliang Xiao, Dong Xue
Summary: A light-promoted Ni-catalyzed cyanation reaction using 1,4-dicyanobenzene as a cyanating agent is described. Various aryl bromides, chlorides, and druglike molecules are converted to their corresponding nitriles (65 examples). Mechanistic studies reveal that under irradiation, the Ni(II)(dtbbpy)(p-C6H4CN)(CN) oxidative addition product undergoes homolytic cleavage of the Ni-aryl bond to generate an aryl radical and a Ni(I)-CN species, which initiates subsequent cyanation reactions.
Article
Chemistry, Organic
Yanling Zhang, Zhiguo Zhang, Yuanyuan Hu, Yunkui Liu, Hongwei Jin, Bingwei Zhou
Summary: We have described a nickel-catalyzed cyanation reaction of aryl/alkenyl halides with alkyl isocyanides. Aryl/alkenyl iodines and bromides were found to be competent electrophiles that reacted with alkyl isocyanides to afford nitrile compounds in moderate to good yields. This protocol features broad functional group tolerance, simple reaction conditions, and gram-scale synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
A. Hess, H. C. Guelen, N. Alandini, A. Mourati, Y. C. Guersoy, P. Knochel
Summary: This study presents a novel method for the selective ortho, ortho'-functionalization of readily available aryl oxazolines using sBu(2)Mg in toluene followed by trapping reactions with electrophiles. The conversions of these nitriles to valuable heterocycles are reported, and a tentative mechanism is proposed for the reactions.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Richa Sharma, Sandeep Chaudhary
Summary: A new method of direct cyanation of N-aryl-(1H/2H)-indazoles via aerobic oxidative C(sp2)-H bond activation has been developed, which shows positional switch by including or excluding AcOH additive, resulting in good to excellent yields with high functional group tolerance. The use of molecular oxygen as a clean and safe oxidant allows for further transformation of the synthesized cyanated product into various other functional groups, showing potential applications in synthetic biology and medicinal chemistry.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Tristan Delcaillau, Adrian Woenckhaus-Alvarez, Bill Morandi
Summary: A nickel-catalyzed cyanation method using Zn(CN)(2) as the cyanide source has been developed for the functionalization of aryl thioethers, involving both C-S bond activation and C-C bond formation. The combination of ligand dcype and base KOAc is crucial for the efficiency of this transformation. The scalability, low catalyst and reagent loadings, and high functional group tolerance make this reaction useful for late-stage derivatization and polymer recycling in organic chemistry.
Article
Chemistry, Applied
Shengyu Wang, Jianqiang Wang, Junyi Pan, Cheng Liu, Xubin Gong, Cheng Guo
Summary: The study introduces an environmentally friendly and cost-effective method for the cyanation of aryl iodides using a combination of catalyst Pd@CeO2, non-toxic cyanide source, and visible light irradiation. The reaction operates at moderate conditions with high yield and good catalytic efficiency. The catalyst shows good reusability and the reaction system displays tolerance to a wide range of functional groups.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Review
Chemistry, Organic
Thaipparambil Aneeja, Cheriya Mukkolakkal Abdulla Afsina, Padinjare Veetil Saranya, Gopinathan Anilkumar
Summary: This review provides an overview of the literature on ruthenium-catalyzed cyanation reactions up to 2021, highlighting their wide application in pharmacology and biology.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Guangzhu Wang, Chaoren Shen, Xinyi Ren, Kaiwu Dong
Summary: An intramolecular Heck cyclization catalyzed by Ni/(S,S)-BDPP was developed for the synthesis of oxindoles with good enantioselectivities. The use of an electrophilic cyanation reagent was found to address the deleterious effect of the coordinative cyanide ion in asymmetric alkene arylcyanation.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Guofu Zhang, Huihui Miao, Chenfei Guan, Chengrong Ding
Summary: The direct transformation of aryl carboxylic acids to aryl nitriles has been achieved through palladium-catalyzed decarbonylative cyanation without the use of a base. Successful analysis of the decarbonylative cyanation of drug molecules and gram-scale reactions validates the practicality and operability of this method.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
