Article
Chemistry, Physical
Sarah B. Pawley, Allyssa M. Conner, Humair M. Omer, Donald A. Watson
Summary: General conditions for the Hiyama-Denmark cross coupling of tetrasubstituted vinyl silanes and aryl halides are reported, enabling the coupling of unactivated vinyl silanes and displaying high stereospecificity. This important discovery simplifies the reaction procedure and reduces the use of toxic additives.
Review
Biochemistry & Molecular Biology
Rida Noor, Ameer Fawad Zahoor, Muhammad Irfan, Syed Makhdoom Hussain, Sajjad Ahmad, Ali Irfan, Katarzyna Kotwica-Mojzych, Mariusz Mojzych
Summary: Hiyama cross-coupling is a versatile reaction that enables the construction of carbon-carbon bonds in synthetic organic chemistry. By coupling organosilicons with organic halides using transition metal catalysts, good yields and high enantioselectivities can be achieved. In recent years, researchers have made significant progress in using the Hiyama coupling reaction for the synthesis of diversified natural products and pharmaceutical drugs.
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)
Article
Chemistry, Organic
Yonghong Liu, Shuangjie Lin, Dandan Zhang, Bingkun Song, Yunhe Jin, Erjun Hao, Lei Shi
Summary: This work presents a photochemical Nozaki-Hiyama-Kishi coupling reaction enabled by bioinspired Hantzsch ester, which serves as both an electron and a proton donor. The method offers a mild and operationally easy approach that shows broad compatibility with various alkenyl triflates and aldehydes.
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, Multidisciplinary
Aurelien Adenot, Lucile Anthore-Dalion, Emmanuel Nicolas, Jean-Claude Berthet, Pierre Thuery, Thibault Cantat
Summary: A new air-tolerant Cu-catalyzed sulfonylative Hiyama cross-coupling reaction for the synthesis of diaryl sulfones has been developed, tolerating a wide range of polar functional groups. Control experiments and DFT calculations elucidated the mechanism involving the formation of a Cu(I)-sulfinate intermediate through fast insertion of a SO2 molecule.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
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
Hai-Peng Gong, Zheng-Jun Quan, Xi-Cun Wang
Summary: An efficient synthesis of C2-aryl pyrimidine derivatives has been developed via Pd-catalyzed Hiyama couplings. The reaction showed good functional group tolerance and the electronic and steric effects of the 2-chloro pyrimidines were negligible for the transformation.
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, 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, Organic
Hao Ye, Ruotong Zhang, Xiaolong Xia, Yue Ding, Meihui Sun, Lei Shi, Guomin Jiang, Xin-Xing Wu
Summary: A palladium-catalyzed domino Heck cyclization/Hiyama cross-coupling has been successfully developed for the synthesis of (hetero)aryl-functionalized azaindoline derivatives bearing all-carbon quaternary centers in moderate to high yields. The synthetic versatility of this method is highlighted by its ability to perform gram-scale synthesis and modification of aryl-containing complex bioactive molecules.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Athmanand Anchi, Shruti S. S. Malunavar, Ravi S. S. Naik, Rajesh G. G. Kalkhambkar, Kenneth K. K. Laali
Summary: The application of conventional and ionic liquid solvents and reagents in the Hiyama cross-coupling reactions using triazenes as coupling partners was studied. Effective and respectable yields were obtained within minutes using microwave-assisted and Pd-catalyzed reactions in various solvents. The IL reagents and solvents were also successfully used to develop stepwise and sequential/tandem Hiyama-Suzuki (H S) and Hiyama-Heck (H H) methods.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
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.
Article
Chemistry, Organic
Yaqun Dong, Song Sun, Jin-tao Yu, Jiang Cheng
TETRAHEDRON LETTERS
(2019)
Article
Chemistry, Organic
Yan Xiao, Song Sun, Jin-Tao Yu, Jiang Cheng
Article
Chemistry, Organic
Song Sun, Cong Zhou, Jiang Cheng
TETRAHEDRON LETTERS
(2019)
Article
Chemistry, Organic
Chang Wang, Peng-Cheng Qian, Fan Chen, Jiang Cheng
TETRAHEDRON LETTERS
(2020)
Article
Chemistry, Organic
Yang Li, Zhixin Wang, Shengbo Xu, Jiang Cheng
TETRAHEDRON LETTERS
(2020)
Article
Chemistry, Organic
Chen Liang, Zhibin Chen, Xinyue Hu, Shengxia Yu, Zhenlian Wang, Jiang Cheng
Summary: We developed a phosphine-catalyzed ring-opening reaction of cyclopropenones with dicarbonyl compounds as C-nucleophiles, leading to 1,3,3'-tricarbonyl compounds. This transition-metal free procedure features mild and neutral reaction conditions with good atom economy, providing an easy pathway to access 1,3,3'-tricarbonyl derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Review
Chemistry, Organic
Lu Wang, Ying Shao, Jiang Cheng
Summary: The cyanation reaction plays a key role in organic chemistry due to the wide applications of nitrile compounds. Traditionally, metal cyanides were used as cyanide sources, but recent research shows the potential of using combined cyanide sources for cyanation reactions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Shengnan Jin, Fan Chen, Pengcheng Qian, Jiang Cheng
Summary: A new method using DTBP as a promoter allows for the difunctionalization of alpha-aryl alpha-alkynyl allylic alcohols with alkyl nitriles, resulting in alpha-alkynyl gamma-cyano functionalized ketones. This process involves C(sp(3))-H bond cleavage of alkyl nitriles and radical 3-exo-dig cyclization, with a preference for 1,2-alkynyl migration over 1,2-aryl migration.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Review
Chemistry, Organic
Chang Wang, Fan Chen, Pengcheng Qian, Jiang Cheng
Summary: The Rh-catalyzed C-H bond activation/annulation provides a new strategy for the synthesis of new frameworks, with important research significance and application prospects.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Chang Wang, Xiaodong Fan, Fan Chen, Peng-Cheng Qian, Jiang Cheng
Summary: A rhodium-catalyzed annulation of vinylene carbonate with amidines was developed in this paper, leading to 4-methylquinazolines with moderate to excellent yields. The procedure proceeded by sequential ortho-acylation and annulation, utilizing vinylene carbonate as the acetylation reagent.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Zhixin Wang, Yang Li, Fan Chen, Peng-Cheng Qian, Jiang Cheng
Summary: A Bronsted acid-promoted intramolecular cyclization reaction was developed in the presence of TsNHNH2 to synthesize polysubstituted indenes with complexity and diversity. Unlike other reactions, a cationic cyclization pathway was involved in this method, where N-tosylhydrazone served as an electrophile and alkylation reagent.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Organic
Cong Zhou, Miao Li, Jintao Yu, Song Sun, Jiang Cheng
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Shanshan Qiao, Peng-Cheng Qian, Fan Chen, Jiang Cheng
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Yaqun Dong, Jin-Tao Yu, Song Sun, Jiang Cheng
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Organic
Yiting Li, Song Sun, Jiang Cheng, Jin-Tao Yu
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
