Article
Chemistry, Organic
Yangyang Weng, Jingping Qu, Yifeng Chen
Summary: This study demonstrates the palladium-catalyzed allylic carbonylative Negishi cross-coupling reaction using sterically bulky aromatic isocyanides as a CO surrogate, leading to β,γ-unsaturated ketones with high regioselectivity and stereoselectivity. The advantages of this method include mild reaction conditions and a wide substrate scope due to the utilization of Negishi reagents as carbon nucleophiles.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Xinlan A. F. Cook, Antoine de Gombert, Janette McKnight, Loic R. E. Pantaine, Michael C. Willis
Summary: This review focuses on the methods developed for the challenging coupling of 2-pyridine nucleophiles with (hetero)aryl electrophiles, ranging from traditional cross-coupling processes to alternative nucleophilic reagents and novel main group approaches.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Organic
Carolina G. S. Lima, Fernanda P. Pauli, Vinicius G. Madriaga, Adriane A. P. Amaral, Isabela A. Graciano, Vinicius L. Meira, Luana da S. M. Forezi, Vitor F. Ferreira, Thiago de M. Lima, Fernando de Carvalho da Silva
Summary: Reactions promoting carbon-carbon bond formation are crucial in organic synthesis, and cross-coupling reactions are commonly used for this purpose. Supramolecular chemistry has emerged as a significant player in this field, offering approaches such as complex structure synthesis, scaffold modification, and repurposing of available materials like agarose. This Review primarily focuses on the development of supramolecular catalysts for Suzuki, Heck, and Sonogashira reactions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Christopher A. Wilhelmsen, Xuntong Zhang, Jesse A. Myhill, James P. Morken
Summary: Versatile beta tert-boryl amides were synthesized through conjunctive cross-coupling of alpha-substituted alkenyl boron ate complexes and carbamoyl chloride electrophiles. The use of a palladium catalyst in combination with MandyPhos enabled enantioselective synthesis. Additionally, the chemoselectivity of the reaction product was enhanced by the addition of water.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Sandra Abi Fayssal, Timothee Naret, Julien Buendia, Axel Labattut, Vincent Huc, Cyril Martini, Emmanuelle Schulz
Summary: This study presented a rapid and scalable synthesis method for supported NHC-Pd(II)-pyridine complexes on a benzyloxycalix[8]arene macrocycle, which were subsequently used in Suzuki-Miyaura benchmark reactions to optimise ligand nature and deliver highly active precatalysts. The insoluble species showed comparable or superior activity to conventional homogeneous catalysts, with the additional benefit of simple filtration post-reaction for low Pd contamination values in target products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Felipe Verdugo, Ricardo Rodino, Martin Calvelo, Jose Luis Mascarenas, Fernando Lopez
Summary: The reactivity of carbonyl-tethered alkylidenecyclopropanes (ACPs) can be directed towards tandem cycloisomerization/cross-coupling processes by using Pd-0 catalysts with phosphorus-based monodentate ligands. This allows for the synthesis of a wide variety of highly functionalized cyclic alcohols and amines through the formation of key pi-allyl oxapalladacyclic intermediates which are trapped with external nucleophilic partners.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Dejiang Zhang, Liyuan Le, Renhua Qiu, Wai-Yeung Wong, Nobuaki Kambe
Summary: A strategy for the formation of antimony-carbon bond via nickel-catalyzed cross-coupling of halostibines was developed. This method has a wide substrate scope and is compatible with various functional groups. The successful synthesis of arylated stibine demonstrated the high synthetic potential of this transformation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Xin Han, Chenxing Guo, Chen Xu, Linlin Shi, Binghui Liu, Zhe Zhang, Qixia Bai, Bo Song, Fangfang Pan, Shuai Lu, Xinju Zhu, Heng Wang, Xin-Qi Hao, Mao-Ping Song, Xiaopeng Li
Summary: We have successfully designed and synthesized two series of metallo-supramolecular octahedral cages based on the self-assembly of modified tripyridyl ligands. These cages have good water solubility and are capable of mediating visible-light-promoted reactions.
Article
Chemistry, Physical
Lukas Hoff, Gleb A. Chesnokov, Anthony Linden, Karl Gademann
Summary: This study presents a thorough mechanistic investigation of the Pd-catalyzed and Ag-mediated cross-coupling reaction between monosubstituted tetrazine and boronic acids. Through kinetic analyses, isolation of intermediates, and computational methods, insights into the mechanism were obtained. The study also demonstrated the experimental confirmation of a highly electron-deficient ligand and the impact of mechanistic understanding on the generality of the reaction scope through a data-driven workflow.
Article
Chemistry, Multidisciplinary
Janette McKnight, Andre Shavnya, Neal W. Sach, David C. Blakemore, Ian B. Moses, Michael C. Willis
Summary: An efficient one-pot desulfinative cross-coupling reaction catalyzed by Pd is reported for the synthesis of medicinally relevant di(hetero)arylmethanes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Physical
Neda Jeddi, Neil W. J. Scott, Ian J. S. Fairlamb
Summary: Recent studies have shown that the privileged reactivity of higher-order metal clusters can be utilized in widely applied catalytic processes. Small Pdn clusters with unique reactivity, selectivity, and catalyst behavior have been discovered, presenting potential in catalyst design and application. This review focuses on the catalytic applications of Pdn clusters and discusses the underlying structure linked to their reactivity. It further proposes a hypothesis regarding the formation of higher-order Pd species through ligated Pdn clusters.
Article
Chemistry, Physical
Neda Jeddi, Neil W. J. Scott, Ian J. S. Fairlamb
Summary: Recent studies have shown that the privileged reactivity of higher-order metal clusters can be utilized in widely applied catalytic processes, such as cross-coupling reactions and hydrogenative transformations. This review focuses on the catalytic applications of Pd-n clusters and discusses the underlying structure of these clusters in relation to their reactivity. It also proposes a hypothesis that ligated Pd-n clusters may play a role in the formation of higher-order Pd species.
Review
Chemistry, Multidisciplinary
Laksmikanta Adak, Takuji Hatakeyama, Masaharu Nakamura
Summary: The recent significant progress in iron-catalyzed cross-coupling reactions has led to competition with well-established nickel and palladium catalyst systems. Iron-catalyzed protocols are advantageous in terms of economy and toxicity, exhibit a wide range of reactivities, and tolerate many functional groups. Development of various iron catalyst systems, including the use of N-heterocyclic carbenes and bisphosphine ligands, has opened up new applications in modern synthetic organic chemistry.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2021)
Article
Multidisciplinary Sciences
Xiao Hai, Yang Zheng, Qi Yu, Na Guo, Shibo Xi, Xiaoxu Zhao, Sharon Mitchell, Xiaohua Luo, Victor Tulus, Mu Wang, Xiaoyu Sheng, Longbin Ren, Xiangdong Long, Jing Li, Peng He, Huihui Lin, Yige Cui, Xinnan Peng, Jiwei Shi, Jie Wu, Chun Zhang, Ruqiang Zou, Gonzalo Guillen-Gosalbez, Javier Perez-Ramirez, Ming Joo Koh, Ye Zhu, Jun Li, Jiong Lu
Summary: Heterogeneous geminal-atom catalysts (GACs) offer a new avenue for the sustainable manufacture of fine chemicals by pairing single-atom sites in specific coordination and spatial proximity.
Article
Chemistry, Physical
Dejiang Zhang, Ting Tang, Zhao Zhang, Liyuan Le, Zhi Xu, Hao Lu, Zhou Tong, Dishu Zeng, Wai-Yeung Wong, Shuang-Feng Yin, Arash Ghaderi, Nobuaki Kambe, Renhua Qiu
Summary: This study presents a general and efficient method for the synthesis of Sb-aryl and Sb-alkyl stibines through nickel-catalyzed cross-coupling reactions with organic halides. The method enables the high selectivity synthesis of complex biaryls and successfully synthesized various molecules, including drugs, with good yields.