Article
Chemistry, Multidisciplinary
Cang Cheng, Xiang Zuo, Dongdong Tu, Bin Wan, Yanghui Zhang
Summary: A method for the synthesis of enantiopure eight-membered nitrogen heterocycles has been developed through diastereoselective cross-coupling of 2-iodobiphenyls with 2-bromobenzylamines. The products provide a new type of chiral scaffold with easy modification and high configurative stability, which could be used in asymmetric synthesis. Palladacycles formed via the C-H activation of 2-iodobiphenyls act as the intermediates, offering a new strategy for synthesizing medium-sized ring compounds.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Inorganic & Nuclear
Li-Hui Hong, Wei-Jung Feng, Wei-Chih Chen, Yu-Chang Chang
Summary: We synthesized a palladium complex (1a) with two different P-donors and proved its effectiveness as a Pd(ii) precatalyst for carbon-phosphorus bond formation. The complex exhibited efficient catalytic activity for the Hirao coupling reaction under environmentally benign conditions. Mechanistic studies were conducted to investigate the generation of plausible Pd(0) active species. The use of bulky di(1-adamantyl)phosphine oxide as a preligand and less bulky di-p-tolylphosphine oxide as the substrate in the coupling reaction was also demonstrated.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Multidisciplinary
Alasdair K. Cooper, Megan E. Greaves, William Donohoe, Paul M. Burton, Thomas O. Ronson, Alan R. Kennedy, David J. Nelson
Summary: A nickel/dppf catalyst system successfully achieved Suzuki-Miyaura cross-coupling reactions of certain chloropyridines and chloroquinolines but not others, due to differences in the reaction mechanism. Chloropyridines rapidly undergo oxidative addition to the catalyst, while alpha-halo-N-heterocycles form catalytically inactive dimeric nickel species.
Article
Chemistry, Multidisciplinary
Rajesh Kancherla, Krishnamoorthy Muralirajan, Sayan Dutta, Kuntal Pal, Bo Li, Bholanath Maity, Luigi Cavallo, Magnus Rueping
Summary: The development of metal complexes that can function as both photocatalysts and cross-coupling catalysts is challenging. This study reports that divalent palladium can act as a light-absorbing species to achieve carbon-nitrogen cross-coupling reactions under air. Palladium acetate can be used as both the photocatalyst and cross-coupling catalyst for the selective cross-coupling amination of differently substituted aryl halides at room temperature.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Lukas Hoff, Simon D. Schnell, Andrea Tomio, Anthony Linden, Karl Gademann
Summary: A silver-mediated Pd-catalyzed cross-coupling method for 3-bromo-1,2,4,5-tetrazine with boronic acids was presented in this study. It was found that electronic modification of the dppf ligand played a crucial role in achieving good turnover. Using this fast method, a variety of alkyl-, heteroatom-, and halide-substituted aryl- and heteroaryl-tetrazines were successfully prepared, with yields up to 87%.
Review
Chemistry, Multidisciplinary
You Wang, Yuli He, Shaolin Zhu
Summary: Migratory cross-coupling via metal migration is a significant process in academic and industrial fields, providing an attractive alternative for the synthesis of challenging structures. This Account outlines recent progress and developments in the field, including migration-functionalization modes, diverse functionalizations, and strategies for regio- and stereocontrol.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Chemistry, Multidisciplinary
Santosh Kumar Sahu, Prabhupada Choudhury, Pradyota Kumar Behera, Tanmayee Bisoyi, Rashmi Ranjan Sahu, Abinash Bisoyi, Koteswara Rao Gorantla, Bhabani S. Mallik, Manoj Mohapatra, Laxmidhar Rout
Summary: The study presents a new protocol for Sonogashira cross-coupling reaction using the cheap and commercially available CuSeO3·2H2O catalyst, resulting in high yields of products under mild conditions without the need for ligands. This marks the first use of an oxygen-bridged copper-based bimetallic catalyst for C-sp-C-sp2 Sonogashira cross-coupling reactions under mild conditions, demonstrating a palladium-free reaction up to a limit of 0.2 ppm.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Sanghyup Seo, Donghyeon Kim, Hyunwoo Kim
Summary: The reductive cross-coupling of terminal alkenes and N-heterocyclic bromides was successfully demonstrated through ligand optimization of Pd and CuH catalysis. The optimized ligands for Pd and CuH catalysis, Briphos and DTB-DPPBz respectively, were further applied to gram-scale production of clathryimine B.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Jin-Chen Li, Bing-Xia Yan, Gang Wang, Zhi-Shi Ye
Summary: Here, we demonstrated an efficient cascade reaction of N-tosyl ortho-alkynylanilines and N-acyl ortho-alkynylanilines using Rh(COD)(2)BF4/( t )BuXantPhos as a catalyst. The reaction exhibited excellent chemoselectivity and regioselectivity, high atom-economy, and wide substrate scope. Mechanistic studies revealed that the success of this reaction relied on the strong capability of the rhodium catalyst to recognize the N-substituent group in the selective nucleophilic cyclization and alkyne insertion.
Article
Chemistry, Organic
Jin-He Na, Xiang Liu, Jia-Wen Jing, Jing Wang, Xue-Qiang Chu, Mengtao Ma, Hao Xu, Xiaocong Zhou, Zhi-Liang Shen
Summary: A step-economical and efficient one-pot reaction was developed for the direct cross-coupling of aryl fluorosulfate with aryl bromide. This reaction, conducted at room temperature in THF solvent, does not require the use of preprepared/commercial organometallic reagents. By utilizing nickel catalyst, magnesium turnings, and lithium chloride, the desired biaryls were obtained in moderate to good yields with reasonable functional group compatibility.
Article
Chemistry, Organic
Hua Yao, Xiaoyang Zhong, Bingqing Wang, Sen Lin, Zhaohua Yan
Summary: A novel and efficient approach for the amine-directed dehydrogenative C(sp(2))-C(sp(3)) coupling of arylamines with acetonitrile was developed using FeCl2 as the catalyst. The method provides a straightforward and green route to arylacetonitriles with good regioselectivity and excellent compatibility of functional groups and aromatic rings.
Article
Chemistry, Multidisciplinary
Ruofei Cheng, Graham de Ruiter, Chao-Jun Li
Summary: Cobalt-based catalysts have shown unique advantages in cross-coupling reactions, with higher catalytic activity and lower toxicity compared to palladium and nickel catalysts. A novel cobalt-catalyzed alkyl-alkyl cross-coupling reaction of hydrazone with alkyl halides has been developed under mild reaction conditions, using a PNP-type pincer ligand as an essential catalyst. Both aldehyde and ketone hydrazones are compatible with this reaction, producing a series of C(sp(3))-C(sp(3)) coupling products in moderate to good yields.
CHEMICAL COMMUNICATIONS
(2022)
Article
Multidisciplinary Sciences
Eiji Shirakawa, Yuki Ota, Kyohei Yonekura, Keisho Okura, Sahiro Mizusawa, Sujan Kumar Sarkar, Manabu Abe
Summary: An electron has been found to catalyze the cross-coupling reaction of organometallic compounds with aryl halides, which is more desirable for green and sustainable chemistry compared to transition metal catalysis. However, high temperature is required for this electron catalysis. We discovered that visible light photoirradiation can accelerate the electron-catalyzed reaction by using photoredox catalysis, enabling the reaction to proceed at room temperature. The supply of the electron catalyst through photoredox catalysis also expands the scope of aryl halides.
Article
Chemistry, Organic
Andrew C. Jones, William I. Nicholson, Jamie A. Leitch, Duncan L. Browne
Summary: The nickel-catalyzed cross-electrophile coupling of aryl halides and alkyl halides enabled by ball-milling is efficient and green, achieving reductive C-C bond formation under a mechanochemical manifold. The mechanical action provided by ball milling allows for the use of a variety of zinc sources to turnover the nickel catalytic cycle, resulting in the synthesis of 28 cross-electrophile coupled products.
Article
Chemistry, Organic
Ying Lin, Liang Zou, Renren Bai, Xiang-Yang Ye, Tian Xie, Yang Ye
Summary: We present an easy and efficient method for vinylation using Fe-catalyzed cross-electrophile coupling of readily available vinyl- and hydro-chlorosilanes with a range of substituted alkenyl bromides using manganese as the terminal reductant. This modular approach allows the formation of various vinyl orgaonosilanes, including electron-rich, electron-poor, and ortho-/meta-/para-substituted vinyl electrophiles, with excellent functional group tolerance and broad substrate scope. Furthermore, this method successfully modified substrates with structurally complex natural products and pharmaceutical motifs, demonstrating its potential in gram-scale reactions and derivatization.
ORGANIC CHEMISTRY FRONTIERS
(2023)
